Organization
Graduate School of Science Professor
Graduate School
Graduate School of Science
Undergraduate School
School of Science Department of Chemistry
Title
Professor
Contact information
SHOJI, Osami
Research Interests
Research Interests 2
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生体関連化学 生物無機化学 蛋白工学 酵素科学
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生体関連化学 生物無機化学 蛋白工学 酵素科学
Research Areas
Research Areas 1
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Others / Others / Chemistry Related to Living Body
Current Research Project and SDGs
Current Research Project and SDGs 1
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ヘム蛋白の機能変換とその制御に関する研究
Research History
Research History 11
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Nagoya University Professor
2019.4
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Nagoya University Graduate School of Science Division of Material Science Inorganic and Analytical Chemistry Professor
2019.4
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Associate professor at Graduate School of Science, Nagoya University
2013.4
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Nagoya University Associate professor
2013.4 - 2019.3
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Country：Japan
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Nagoya University Graduate School of Science Division of Material Science Inorganic and Analytical Chemistry Associate professor
2013.4 - 2019.3
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Nagoya University Assistant Professor
2008.10 - 2013.3
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Country：Japan
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Assistant Professor at Research Center for Materials Science, Nagoya University
2007.12 - 2008.9
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Country：Japan
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JSPS Postdoctoral fellow
2006.4 - 2007.11
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Country：Japan
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Postdoctoral fellow at Research Center for Materials Science, Nagoya University
2005.4 - 2006.3
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Country：Japan
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Postdoctoral fellow at Graduate School of Materials Science, Nara Institute of Science and Technology, Nara, Japan
2004.4 - 2005.3
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Country：Japan
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Postdoctoral fellow of the Core Research for Evolutional Science and Technology (CREST) project of Japan Science and Technology Agency (JST)
2002.4 - 2004.3
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Country：Japan
Education
Education 3
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Chiba University Graduate School, Division of National Science and Technology Graduate school of Science and Technology
1999.4 - 2002.3
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Country： Japan
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Chiba University Graduate School, Division of National Science and Technology Graduate School of Science and Technology
1997.4 - 1999.3
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Country： Japan
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Chiba University Faculty of Engineering Department of Applied Chemistry
1993.4 - 1997.3
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Country： Japan
Professional Memberships
Professional Memberships 10
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The Chemical Society of Japan
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Division of biofunctional chemistry, The Chemical Society of Japan
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Japan Society of Coordination Chemistry
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The Society of Polymer Science, Japan
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American Chemical Society
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The Society of Polymer Science, Japan
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Japan Society of Coordination Chemistry
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Division of biofunctional chemistry, The Chemical Society of Japan
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The Chemical Society of Japan
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American Chemical Society
Committee Memberships
Committee Memberships 1
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緑膿菌感染症研究会 運営委員
2021.4
Awards
Awards 5
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日本化学会第93回春季年会 第27回若い世代の特別講演会賞
2013.3 日本化学会
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Country：Japan
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第5回バイオ関連化学シンポジウム講演賞
2011.9 生体機能関連化学部会
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Country：Japan
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Poster award from 16th International Conference on Cytochrome P450
2009.7 16th International Conference on Cytochrome P450
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Country：Japan
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EXCELLENT LECTURE AWARD from the Chemical Society of Japan
2007.5 The Chemical Society of Japan
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Country：Japan
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NANOHANA VENTURE AWARD
2000.12 Center for Electronics and Photonics Chiba University-Venture Business Laboratory
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Country：Japan
Papers
Papers 86
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XFEL crystallography reveals catalytic cycle dynamics during non-native substrate oxidation by cytochrome P450BM3 Reviewed Open Access
Satoshi Nagao, Wako Kuwano, Takehiko Tosha, Keitaro Yamashita, Joshua Kyle Stanfield, Chie Kasai, Shinya Ariyasu, Kunio Hirata, Go Ueno, Hironori Murakami, Hideo Ago, Masaki Yamamoto, Osami Shoji, Hiroshi Sugimoto, Minoru Kubo
Communications Chemistry 2025.3
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Bacterial acyl homoserine lactones triggered non‐native substrate hydroxylation catalysed by directed‐evolution‐derived cytochrome P450BM3 mutants Open Access
Yuya Yokoyama, Shinya Ariyasu, Masayuki Karasawa, Chie Kasai, Yuichiro Aiba, Hiroshi Sugimoto, Osami Shoji
ChemCatChem 2024.10
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Publishing type：Research paper (scientific journal) Publisher：Wiley
We report the directed evolution of cytochrome P450BM3 to efficiently utilise the bacterial quorum sensing signalling molecule N‐decanoyl homoserine lactone (C10‐HSL) as an effective decoy molecule. This represents the first important step in our endeavour to develop of a self‐sufficient decoy‐molecule system in whole‐cells that only necessitates the addition of culture medium and substrate to realise the hydroxylation of non‐native substrates. Following five rounds of directed evolution, mutant P450BM3, in the presence of C10‐HSL, catalysed the hydroxylation of benzene at a rate of 475 min−1, the highest turnover rate recorded for any P450 enzyme, and achieving a 46% yield in a whole‐cell reaction system. High‐resolution X‐ray crystal structure analysis of a series of mutants narrates the directed evolution process, revealing how C10‐HSL is fixed in the binding pocket to permit binding of non‐native substrates. Finally, introduction of the C10‐HSL synthase gene ExpI into E. coli, enabled the in‐situ production of C10‐HSL, realising, for the first time, the hydroxylation of non‐native substrates without the need for the laborious synthesis and addition of decoy molecules.
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Influence of Solvents on Catalytic C–H Bond Oxidation by a Copper(II)–Alkylperoxo Complex Reviewed International coauthorship
Yuri Lee, Bohee Kim, Seonghan Kim, Elvis Wang Hei Ng, Shinya Ariyasu, Osami Shoji, Sungho Yoon, Hajime Hirao, Jaeheung Cho
ACS Catalysis Vol. 14 ( 5 ) page： 3524 - 3532 2024.2
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Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society (ACS)
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Hiroaki Inaba, Yuma Shisaka, Shinya Ariyasu, Erika Sakakibara, Garyo Ueda, Yuichiro Aiba, Nobutaka Shimizu, Hiroshi Sugimoto, Osami Shoji
RSC Advances Vol. 14 ( 13 ) page： 8829 - 8836 2024
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)
Construction of a bevel-gear-like protein assembly using a synthetic porphyrin with defined flexibility.
DOI： 10.1039/d4ra01042f
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Investigating the applicability of the CYP102A1-decoy-molecule system to other members of the CYP102A subfamily Reviewed
Joshua Kyle Stanfield, Hiroki Onoda, Shinya Ariyasu, Chie Kasai, Eleanor Mary Burfoot, Hiroshi Sugimoto, Osami Shoji
Journal of Inorganic Biochemistry Vol. 245 page： 112235 - 112235 2023.8
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Elsevier {BV}
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Shinya Ariyasu, Kai Yonemura, Chie Kasai, Yuichiro Aiba, Hiroki Onoda, Yuma Shisaka, Hiroshi Sugimoto, Takehiko Tosha, Minoru Kubo, Takashi Kamachi, Kazunari Yoshizawa, Osami Shoji
ACS Catalysis page： 8613 - 8623 2023.6
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society (ACS)
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Construction of Biocatalysts Using the P450 Scaffold for the Synthesis of Indigo from Indole. Reviewed International coauthorship International journal
Yanqing Li, Yingwu Lin, Fang Wang, Jinghan Wang, Osami Shoji, Jiakun Xu
International journal of molecular sciences Vol. 24 ( 3 ) 2023.1
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Language：English Publishing type：Research paper (scientific journal)
With the increasing demand for blue dyes, it is of vital importance to develop a green and efficient biocatalyst to produce indigo. This study constructed a hydrogen peroxide-dependent catalytic system for the direct conversion of indole to indigo using P450BM3 with the assistance of dual-functional small molecules (DFSM). The arrangements of amino acids at 78, 87, and 268 positions influenced the catalytic activity. F87G/T268V mutant gave the highest catalytic activity with kcat of 1402 min-1 and with a yield of 73%. F87A/T268V mutant was found to produce the indigo product with chemoselectivity as high as 80%. Moreover, F87G/T268A mutant was found to efficiently catalyze indole oxidation with higher activity (kcat/Km = 1388 mM-1 min-1) than other enzymes, such as the NADPH-dependent P450BM3 (2.4-fold), the Ngb (32-fold) and the Mb (117-fold). Computer simulation results indicate that the arrangements of amino acid residues in the active site can significantly affect the catalytic activity of the protein. The DFSM-facilitated P450BM3 peroxygenase system provides an alternative, simple approach for a key step in the bioproduction of indigo.
DOI： 10.3390/ijms24032395
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A Compound I Mimic Reveals the Transient Active Species of a Cytochrome P450 Enzyme: Insight into the Stereoselectivity of P450-Catalysed Oxidations Reviewed
Kazuto Suzuki, Joshua Kyle Stanfield, Keita Omura, Yuma Shisaka, Shinya Ariyasu, Chie Kasai, Yuichiro Aiba, Hiroshi Sugimoto, Osami Shoji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2023.1
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH
Catching the structure of cytochrome P450 enzymes in flagrante is crucial for the development of P450 biocatalysts, as most structures collected are found trapped in a precatalytic conformation. At the heart of P450 catalysis lies Cpd I, a short-lived, highly reactive intermediate, whose recalcitrant nature has thwarted most attempts at capturing catalytically relevant poses of P450s. We report the crystal structure of P450BM3 mimicking the state in the precise moment preceding epoxidation, which is in perfect agreement with the experimentally observed stereoselectivity. This structure was attained by incorporation of the stable Cpd I mimic oxomolybdenum mesoporphyrin IX into P450BM3 in the presence of styrene. The orientation of styrene to the Mo-oxo species in the crystal structures sheds light onto the dynamics involved in the rotation of styrene to present its vinyl group to Cpd I. This method serves as a powerful tool for predicting and modelling the stereoselectivity of P450 reactions.
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Highly selective hydroxylation of gaseous alkanes at the terminal position by wild-type CYP153A33 Open Access
Yusaku Kodama, Shinya Ariyasu, Masayuki Karasawa, Yuichiro Aiba, Osami Shoji
Catalysis Science & Technology Vol. 13 ( 21 ) page： 6146 - 6152 2023
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Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)
Highly regioselective hydroxylation of propane at the terminal position has been achieved using CYP153A33 with decoy molecules. This combination can exhibit the ability to hydroxylate ethane and methane.
DOI： 10.1039/d3cy00752a
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Tetraphenylporphyrin Enters the Ring: First Example of a Complex between Highly Bulky Porphyrins and a Protein. Reviewed International journal
Yuma Shisaka, Erika Sakakibara, Kazuto Suzuki, Joshua Kyle Stanfield, Hiroki Onoda, Garyo Ueda, Miu Hatano, Hiroshi Sugimoto, Osami Shoji
Chembiochem : a European journal of chemical biology Vol. 23 ( 14 ) page： e202200095 2022.7
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
Tetraphenylporphyrin (TPP) is a symmetrically substituted synthetic porphyrin whose properties can be readily modified, providing it with significant advantages over naturally occurring porphyrins. Herein, we report the first example of a stable complex between a native biomolecule, the haemoprotein HasA, and TPP as well as its derivatives. The X-ray crystal structures of nine different HasA-TPP complexes were solved at high resolutions. HasA capturing TPP derivatives was also demonstrated to inhibit growth of the opportunistic pathogen Pseudomonas aeruginosa. Mutant variants of HasA binding FeTPP were shown to possess a different mode of coordination, permitting the cyclopropanation of styrene.
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Natural and artificial enzymes and medicinal aspects: general discussion. Invited Reviewed International journal
Philip Ash, Akhil R Chakravarty, Peter Comba, Abhishek Dey, Debabrata Goswami, Christof Martin Jäger, Kenneth Karlin, Subrata Kundu, Salvatore La Gatta, Rocío López Domene, Jean-Didier Maréchal, Shyamalava Mazumdar, Govindasamy Mugesh, Dimitrios Pantazis, Anca Pordea, Peter J Sadler, Volker Schünemann, Sayam Sen Gupta, Osami Shoji, Edward I Solomon, Paul Walton, Juliusz A Wolny
Faraday discussions Vol. 234 page： 367 - 387 2022.5
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
DOI： 10.1039/d2fd90014a
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A Heme-Acquisition Protein Reconstructed with a Cobalt 5-Oxaporphyrinium Cation and Its Growth-Inhibition Activity Toward Multidrug-Resistant Pseudomonas aeruginosa Reviewed
Takiguchi Asahi, Sakakibara Erika, Sugimoto Hiroshi, Shoji Osami, Shinokubo Hiroshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 61 ( 7 ) 2022.2
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal)
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Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3-Based Whole-Cell Biocatalyst. International journal
Masayuki Karasawa, Kai Yonemura, Joshua Kyle Stanfield, Kazuto Suzuki, Osami Shoji
Angewandte Chemie (International ed. in English) Vol. 61 ( 7 ) page： e202111612 2022.2
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal)
We report an OmpF loop deletion mutant, which improves the cellular uptake of external additives into an Escherichia coli whole-cell biocatalyst. Through co-expression of the OmpF mutant with wild-type P450BM3 in the presence of decoy molecules, the yield of the whole-cell biotransformation of benzene could be considerably improved. Notably, with the decoy molecule C7AM-Pip-Phe the yield duodecupled from 5.7 % to 70 %, with 80 % phenol selectivity. The benzylic hydroxylation of alkyl- and cycloalkylbenzenes was also examined, and with the aid of decoy molecules, propylbenzene and tetralin were converted to 1-hydroxylated products with 78 % yield and 94 % (R) ee for propylbenzene and 92 % yield and 94 % (S) ee for tetralin. Our results suggest that both the decoy molecule and substrate traverse the artificial OmpF channel, synergistically boosting whole-cell bioconversions.
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Heme-containing proteins: Structures, functions, and engineering Invited Reviewed
Osami Shoji, Yuichiro Aiba, Shinya Ariyasu, Hiroki Onoda
Reference Module in Chemistry, Molecular Sciences and Chemical Engineering page： 194 - 214 2022
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Authorship：Corresponding author Language：English Publishing type：Research paper (other academic) Publisher：Elsevier
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Gaseous Alkane Hydroxylation by Deceiving Cytochrome P450BM3 Using Decoy Molecules Invited Reviewed
Joshua Kyle Stanfield, Osami Shoji
JOURNAL OF THE JAPAN PETROLEUM INSTITUTE Vol. 65 ( 3 ) page： 79 - 87 2022
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Authorship：Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：JAPAN PETROLEUM INST
Cytochrome P450BM3 (P450BM3) catalyses the monooxygenation of fatty acids. However, in the case of non-native substrates possessing different structures from fatty acids, P450BM3 remains in an inactive state and catalysis does not proceed. This review will introduce a unique approach, wherein native substrate mimics (decoy molecules) are employed to trick P450BM3 into mistakenly hydroxylating non-native substrates. The decoy molecule system has the advantage that wild-type enzyme can be employed and catalytic activity improved by developing appropriate decoy molecules. With a focus on the hydroxylation of gaseous alkanes, key developments since the first discovery of decoy molecules to the present day will be covered briefly herein. Notably, ethane was efficiently hydroxylated by wild-type P450BM3 with assistance of the systematically evolved N-substituted dipeptidic decoy molecule N-enanthoyl-L-pipecolyl-L-phenylalanine (C7AMPipPhe), achieving a TOF of 82.7 min(-1) P450(-1), representing the highest TOF among reported values catalysed by P450s including engineered P450s.
DOI： 10.1627/jpi.65.79
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The Power of Deception: Using Decoy Molecules to Manipulate P450BM3 Biotransformations Invited Reviewed
Stanfield Joshua Kyle, Shoji Osami
CHEMISTRY LETTERS Vol. 50 ( 12 ) page： 2025 - 2031 2021.12
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal)
DOI： 10.1246/cl.210584
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Exploring hitherto uninvestigated reactions of the fatty acid peroxygenase CYP152A1: catalase reaction and Compound I formation Invited Reviewed
Onoda Hiroki, Tanaka Shota, Watanabe Yoshihito, Shoji Osami
FARADAY DISCUSSIONS 2021.10
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal)
DOI： 10.1039/d1fd00065a
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C9orf72-derived arginine-rich poly-dipeptides impede phase modifiers Reviewed
Nanaura Hitoki, Kawamukai Honoka, Fujiwara Ayano, Uehara Takeru, Aiba Yuichiro, Nakanishi Mari, Shiota Tomo, Hibino Masaki, Wiriyasermkul Pattama, Kikuchi Sotaro, Nagata Riko, Matsubayashi Masaya, Shinkai Yoichi, Niwa Tatsuya, Mannen Taro, Morikawa Naritaka, Iguchi Naohiko, Kiriyama Takao, Morishima Ken, Inoue Rintaro, Sugiyama Masaaki, Oda Takashi, Kodera Noriyuki, Toma-Fukai Sachiko, Sato Mamoru, Taguchi Hideki, Nagamori Shushi, Shoji Osami, Ishimori Koichiro, Matsumura Hiroyoshi, Sugie Kazuma, Saio Tomohide, Yoshizawa Takuya, Mori Eiichiro
NATURE COMMUNICATIONS Vol. 12 ( 1 ) 2021.9
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Language：Japanese Publishing type：Research paper (scientific journal)
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Short-lived intermediate in N2O generation by P450 NO reductase captured by time-resolved IR spectroscopy and XFEL crystallography Reviewed
Nomura Takashi, Kimura Tetsunari, Kanematsu Yusuke, Yamada Daichi, Yamashita Keitaro, Hirata Kunio, Ueno Go, Murakami Hironori, Hisano Tamao, Yamagiwa Raika, Takeda Hanae, Gopalasingam Chai, Kousaka Ryota, Yanagisawa Sachiko, Shoji Osami, Kumasaka Takashi, Yamamoto Masaki, Takano Yu, Sugimoto Hiroshi, Tosha Takehiko, Kubo Minoru, Shiro Yoshitsugu
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA Vol. 118 ( 21 ) 2021.5
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Language：Japanese Publishing type：Research paper (scientific journal)
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TRICKING CYTOCHROME P450BM3: CATALYSIS OF VARIOUS NON-NATIVE SUBSTRATE TRANSFORMATIONS USING DECOY MOLECULES Reviewed
Joshua K. Stanfield, Kazuto Suzuki, Kai Yonemura, Talita Malewschik, Osami Shoji
QUIMICA NOVA Vol. 44 ( 8 ) page： 982 - 998 2021
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Authorship：Corresponding author Language：Portuguese Publishing type：Research paper (scientific journal) Publisher：SOC BRASILEIRA QUIMICA
In order to accomplish a greener chemistry, enzymes, such as the fatty-acid hydroxylase cytochrome P450BM3, have garnered increasing attention as potential candidates for the development of potent biocatalysts in recent years. However, one of the biggest issues hampering the quick and efficient application of P450BM3 as a biocatalyst lies in its stringent substrate specificity. Consequently, diverse mutagenesis-based approaches have been successfully employed as a means to alter the substrate specificity of P450BM3, leading to the generation of a myriad of highly specialised mutant variants. Nevertheless, repeated exhaustive mutagenesis is a laborious process with no guarantee for success, thus, alternative methods to more easily alter the enzyme's substrate specificity have become increasingly desirable. In recent years, decoy molecules, which possess the ability to deceive wild-type P450BM3 into hydroxylating a range of non-native substrates, have emerged as such a "simpler" alternative. Within this review, focus will be placed upon the process underlying the development of these decoy molecules, which will be discussed in great detail. Furthermore, a summary of recent developments pertaining to the potential applications of decoy molecules from the development of a whole-cell biocatalyst to their use in crystallography will be discussed.
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Investigation of the Characteristics of NLS-PNA: Influence of NLS Location on Invasion Efficiency Reviewed
Aiba Yuichiro, Urbina Gerardo, Shibata Masanari, Shoji Osami
APPLIED SCIENCES-BASEL Vol. 10 ( 23 ) page： 8663 2020.12
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Expanding the applicability of cytochrome P450s and other haemoproteins Invited Reviewed
Shinya Ariyasu, Joshua Kyle Stanfield, Yuichiro Aiba, Osami Shoji
Current Opinion in Chemical Biology Vol. 59 page： 155 - 163 2020.12
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Elsevier BV
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Iron(III) 5,15-Diazaporphyrin Catalysts for the Direct Oxidation of C(sp3)–H Bonds Reviewed
Tsubasa Nishimura, Takahisa Ikeue, Osami Shoji, Hiroshi Shinokubo, Yoshihiro Miyake
Inorganic Chemistry Vol. 59 ( 21 ) page： 15751 - 15756 2020.11
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Language：Japanese Publishing type：Research paper (scientific journal) Publisher：American Chemical Society ({ACS})
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Enhanced cis- and enantioselective cyclopropanation of styrene catalysed by cytochrome P450BM3 using decoy molecules Reviewed
Kazuto Suzuki, Yuma Shisaka, Joshua Kyle Stanfield, Yoshihito Watanabe, Osami Shoji
Chemical Communications Vol. 56 ( 75 ) page： 11026 - 11029 2020.9
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry ({RSC})
DOI： 10.1039/d0cc04883f
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Kai Yonemura, Shinya Ariyasu, Joshua Kyle Stanfield, Kazuto Suzuki, Hiroki Onoda, Chie Kasai, Hiroshi Sugimoto, Yuichiro Aiba, Yoshihito Watanabe, Osami Shoji
ACS Catalysis Vol. 10 ( 16 ) page： 9136 - 9144 2020.8
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：American Chemical Society (ACS)
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Control of microenvironment around enzymes by hydrogels Reviewed
Yuichiro Kobayashi, Kenji Kohara, Yusuke Kiuchi, Hiroki Onoda, Osami Shoji, Hiroyasu Yamaguchi
Chemical Communications Vol. 56 ( 49 ) page： 6723 - 6726 2020.6
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Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)
<p>The oxidation of substrates by P450 is regulated by introducing an interaction site with decoy molecules into polymer hydrogels.</p>
DOI： 10.1039/d0cc01332c
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Joshua Kyle Stanfield, Keita Omura, Ayaka Matsumoto, Chie Kasai, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie International Edition Vol. 59 ( 19 ) page： 7611 - 7618 2020.5
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Wiley
Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.201913407
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Kristalle in Minutenschnelle: Sofortige Mikrokristallisation verschiedenster Varianten der CYP102A1‐(P450BM3)‐Hämdomäne Reviewed
Joshua Kyle Stanfield, Keita Omura, Ayaka Matsumoto, Chie Kasai, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie Vol. 132 ( 19 ) page： 7681 - 7689 2020.5
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Authorship：Corresponding author Language：German Publishing type：Research paper (scientific journal) Publisher：Wiley
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Cationic guanine: positively charged nucleobase with improved DNA affinity inhibits self-duplex formation Reviewed
Masaki Hibino, Yuichiro Aiba, Osami Shoji
Chemical Communications Vol. 56 ( 17 ) page： 2546 - 2549 2020.2
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry ({RSC})
DOI： 10.1039/d0cc00169d
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Shinya Ariyasu, Yusaku Kodama, Chie Kasai, Zhiqi Cong, Joshua Kyle Stanfield, Yuichiro Aiba, Yoshihito Watanabe, Osami Shoji
ChemCatChem Vol. 11 ( 19 ) page： 4709 - 4714 2019.10
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Authorship：Corresponding author Language：Japanese Publishing type：Research paper (scientific journal) Publisher：Wiley
Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cctc.201901323
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Hijacking the Heme Acquisition System of Pseudomonas aeruginosa for the Delivery of Phthalocyanine as an Antimicrobial Reviewed
Shisaka Yuma, Iwai Yusuke, Yamada Shiho, Uehara Hiromu, Tosha Takehiko, Sugimoto Hiroshi, Shiro Yoshitsugu, Stanfield Joshua K, Ogawa Kazuya, Watanabe Yoshihito, Shoji Osami
ACS CHEMICAL BIOLOGY Vol. 14 ( 7 ) page： 1637 - 1642 2019.7
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Language：Japanese Publishing type：Research paper (scientific journal)
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Highly malleable haem-binding site of the haemoprotein HasA permits stable accommodation of bulky tetraphenylporphycenes Reviewed
Sakakibara Erika, Shisaka Yuma, Onoda Hiroki, Koga Daiki, Xu Ning, Ono Toshikazu, Hisaeda Yoshio, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito, Shoji Osami
RSC ADVANCES Vol. 9 ( 32 ) page： 18697 - 18702 2019.6
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The effect of decoy molecules on the activity of the P450Bm3 holoenzyme and a heme domain peroxygenase variant Reviewed
Dezvarei Shaghayegh, Shoji Osami, Watanabe Yoshihito, Bell Stephen G
CATALYSIS COMMUNICATIONS Vol. 124 page： 97 - 102 2019.5
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Language：Japanese Publishing type：Research paper (scientific journal)
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Hoodwinking Cytochrome P450BM3 into Hydroxylating Non-Native Substrates by Exploiting Its Substrate Misrecognition Reviewed
Osami Shoji, Yuichiro Aiba, Yoshihito Watanabe
Accounts of Chemical Research Vol. 52 ( 4 ) page： 925 - 934 2019.4
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Language：Japanese Publishing type：Research paper (scientific journal) Publisher：American Chemical Society ({ACS})
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Frontispiece: Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives Reviewed
Masayuki Karasawa, Joshua Kyle Stanfield, Sota Yanagisawa, Osami Shoji, Yoshihito Watanabe
Angewandte Chemie International Edition Vol. 57 ( 38 ) page： 12264-12269 2018.9
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Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley
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Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives
Masayuki Karasawa, Joshua Kyle Stanfield, Sota Yanagisawa, Osami Shoji, Yoshihito Watanabe
Angewandte Chemie International Edition Vol. 57 ( 38 ) page： 12264 - 12269 2018.9
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Frontispiz: Ganzzellbiotransformation von Benzol zu Phenol durch intrazelluläres Zytochrom P450BM3 aktiviert mithilfe externer Zusätze
Masayuki Karasawa, Joshua Kyle Stanfield, Sota Yanagisawa, Osami Shoji, Yoshihito Watanabe
Angewandte Chemie Vol. 130 ( 38 ) page： 12444 - 12449 2018.9
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Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives Reviewed
M. Karasawa, J. K. Stanfield, S. Yanagisawa, O. Shoji, Y. Watanabe
Angew. Chem. Int. Ed. Vol. 57 page： 12264-12269 2018.9
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Language：English Publishing type：Research paper (scientific journal)
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Peptide Nucleic Acid Conjugated with Ruthenium-Complex Stabilizing Double-Duplex Invasion Complex Even under Physiological Conditions Reviewed
Masaki Hibino, Yuichiro Aiba, Yoshihito Watanabe, Osami Shoji
ChemBioChem Vol. 19 ( 15 ) page： 1601-1604 2018.8
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Language：English Publishing type：Research paper (scientific journal) Publisher：Wiley
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Metabolic enhancement of 2,3´,4,4´,5-pentachlorobiphenyl (CB118) using cytochrome P450 monooxygenase isolated from soil bacterium under the presence of perfluorocarboxylic acids (PFCAs) and the structural basis of its metabolism Reviewed International journal
E. Goto, Y. Haga, M. Kubo, T. Itoh, C. Kasai, O. Shoji, K. Yamamoto, C. Matsumura, T. Nakano, H. Inui
Chemosphere Vol. 210 page： 376-383 - 383 2018.7
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2,3',4,4',5-Pentachlorobiphenyl (CB118) is one of the most abundant polychlorinated biphenyl (PCB) congeners in the environment, and perfluoroalkyl acids, including perfluorocarboxylic acids (PFCAs), are widely distributed in the environment. Although CB118 and perfluoroalkyl acids are present in all humans and biota, effects in the metabolic fate of CB118 leading to toxicity change are unclear. P450BM3, which is isolated from the soil bacterium Bacillus megaterium, metabolized CB118 to three different hydroxylated pentachlorobiphenyls (M1-M3). M2 was identified as 4'-OH-2,3',4,5,5'-pentachlorobiphenyl. These reactions were promoted by the presence of PFCAs, and perfluorooctanoic acid (PFCA-C8) was the most effective for accelerating these reactions among PFCAs with different carbon chain length. The production rate of M2 was accelerated by 25-times using PFCA-C8. Furthermore, the docking models of P450BM3 with CB118 and PFCAs revealed that the conformational changes of the substrate-binding cavity of P450BM3 after binding of PFCAs to P450BM3 were important for selective production of CB118 metabolites. This study leads to the clarification of the different metabolic fates of PCBs under complex contamination with PFCAs.
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Dual-Functional Small Molecules for Generating an Efficient Cytochrome P450BM3 Peroxygenase Reviewed
Nana Ma, Zhifeng Chen, Jie Chen, Jingfei Chen, Cong Wang, Haifeng Zhou, Lishan Yao, Osami Shoji, Yoshihito Watanabe, Zhiqi Cong
Angewandte Chemie - International Edition Vol. 57 ( 26 ) page： 7628 - 7633 2018.6
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We report a unique strategy for the development of a H2O2-dependent cytochrome P450BM3 system, which catalyzes the monooxygenation of non-native substrates with the assistance of dual-functional small molecules (DFSMs), such as N-(ω-imidazolyl fatty acyl)-l-amino acids. The acyl amino acid group of DFSM is responsible for bounding to enzyme as an anchoring group, while the imidazolyl group plays the role of general acid–base catalyst in the activation of H2O2. This system affords the best peroxygenase activity for the epoxidation of styrene, sulfoxidation of thioanisole, and hydroxylation of ethylbenzene among those P450–H2O2 system previously reported. This work provides the first example of the activation of the normally H2O2-inert P450s through the introduction of an exogenous small molecule. This approach improves the potential use of P450s in organic synthesis as it avoids the expensive consumption of the reduced nicotinamide cofactor NAD(P)H and its dependent electron transport system. This introduces a promising approach for exploiting enzyme activity and function based on direct chemical intervention in the catalytic process.
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Hydroxylation of gaseous alkanes and benzene catalyzed by cytochrome P450BM3 using decoy molecules as a substrate analogue
Shoji Osami, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Switchable stereoselectivity in monooxygenation of non-native substrates by P450BM3 using decoy molecules
Suzuki Kazuto, Shoji Osami, Stanfield Joshua, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Hydroxylation of gaseous alkanes and benzene catalyzed by cytochrome P450BM3 using decoy molecules as a substrate analogue
Shoji Osami, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Switchable stereoselectivity in monooxygenation of non-native substrates by P450BM3 using decoy molecules
Suzuki Kazuto, Shoji Osami, Stanfield Joshua, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Efficient hydroxylation of cycloalkanes by co-addition of decoy molecules to variants of the cytochrome P450 CYP102A1 Reviewed
S. Dezvarei, H. Onoda, O. Shoji, Y. Watanabe, S. G. Bell
J. Inorg. Biochem. Vol. 183 page： 137-145 2018.3
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α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids Reviewed
Hiroki Onoda, Osami Shoji, Kazuto Suzuki, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
Catalysis Science & Technology Vol. 8 ( 2 ) page： 434 - 442 2018
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Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H2O2. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H2O2 concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H2O2 (1-10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An 18O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H2O2 to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.
DOI： 10.1039/C7CY02263H
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Reconstitution of full-length P450BM3 with an artificial metal complex by utilising the transpeptidase Sortase A Reviewed International journal
Keita Omura, Yuichiro Aiba, Hiroki Onoda, Joshua Kyle Stanfield, Shinya Ariyasu, Hiroshi Sugimoto, Yoshitsugu Shiro, Osami Shoji, Yoshihito Watanabe
Chemical Communications Vol. 54 ( 57 ) page： 7892-7895 - 7895 2018
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Haem substitution is an effective approach to tweak the function of haemoproteins. Herein, we report a facile haem substitution method for self-sufficient cytochrome P450BM3 (CYP102A1) from Bacillus megaterium utilising the transpeptidase Sortase A from Staphylococcus aureus. We successfully constructed Mn-substituted BM3 and investigated its catalytic activity.
DOI： 10.1039/C8CC02760A
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Structures of the Heme Acquisition Protein HasA with Iron(III)-5,15-Diphenylporphyrin and Derivatives Thereof as an Artificial Prosthetic Group Reviewed
Hiromu Uehara, Yuma Shisaka, Tsubasa Nishimura, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihiro Miyake, Hiroshi Shinokubo, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie International Edition Vol. 56 ( 48 ) page： 15279 - 15283 2017.11
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Hiromu Uehara, Yuma Shisaka, Tsubasa Nishimura, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihiro Miyake, Hiroshi Shinokubo, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie Vol. 129 ( 48 ) page： 15675 - 15675 2017.11
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Capturing an initial intermediate during the P450nor enzymatic reaction using time-resolved XFEL crystallography and caged-substrate Reviewed
T.Tosha, T. Nomura, T. Nishida, N. Saeki, K. Okubayashi, R. Yamagiwa, M. Sugahara, T. Nakane, K. Yamashita, K. Hirata, G. Ueno, T. Kimura, T. Hisano, K. Muramoto, H. Sawai, H. Takeda, E. Mizohata, A. Yamashita, Y. Kanematsu, Y. Takano, E. Nango, R. Tanaka, O. Nureki, O. Shoji, Y. Ikemoto, H. Murakami, S. Owada, K. Tono, M. Yabashi, M. Yamamoto, H. Ago, S. Iwata, H. Sugimoto, Y. Shiro, M. Kubo
Nature Communications Vol. 8 ( 1 ) page： 1585 2017.11
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Inhibiting Aggregation of β-Amyloid by Folded and Unfolded Forms of Fimbrial Protein of Gram-Negative Bacteria Reviewed
K. Yamamoto, M. Oyaizu, T. Takahashi, Y. Watanabe, O. Shoji
Chemistry Select Vol. 2 ( 28 ) page： 9058-9062 2017.10
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Monooxygenation of Nonnative Substrates Catalyzed by Bacterial Cytochrome P450s Facilitated by Decoy Molecules Reviewed
O. Shoji, Y. Watanabe
Chemistry Letters Vol. 46 ( 3 ) page： 278-288 2017.3
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DOI： 10.1246/cl.160963
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Use of apomyoglobin to gently remove heme from a H2O2-dependent cytochrome P450 and allow its reconstitution
Shih-Cheng Chien, Osami Shoji, Yoshiko Morimoto, Yoshihito Watanabe
NEW JOURNAL OF CHEMISTRY Vol. 41 ( 1 ) page： 302 - 307 2017.1
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The heme of hydrogen peroxide-dependent cytochrome P450(BS beta) (P450(BS beta)) was removed by apomyoglobin under mild conditions to give apo-P450(BS beta) without the need for acidic conditions and organic solvents. The circular dichroism spectrum of the apo-P450(BS beta) was essentially identical to that of holo-P450(BS beta), showing a small structural change resulting from the removal of heme using apomyoglobin. The apo-P450(BS beta) was reconstituted with hemin or manganese protoporphyrin IX (MnPPIX), and the resulting reconstituted P450(BS beta) catalyzed the one-electron oxidation of guaiacol using hydrogen peroxide as an oxidant. A higher catalytic activity was observed for P450(BS beta) reconstituted with MnPPIX when meta-chloroperoxybenzoic acid (mCPBA) was used as the oxidant.
DOI： 10.1039/c6nj02882a
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Suzuki, K., Stanfield, J.K., Shoji, O., Yanagisawa, S., Sugimoto, H., Shiro, Y., Watanabe, Y.
Catalysis Science and Technology Vol. 7 ( 15 ) page： 3332 - 3338 2017
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The hydroxylation of non-native substrates catalysed by wild-type P450BM3 is reported, wherein "decoy molecules", i.e., native substrate mimics, controlled the stereoselectivity of hydroxylation reactions. We employed decoy molecules with diverse structures, resulting in either a significant improvement in enantio-selectivity or clear inversion of stereoselectivity in the benzylic hydroxylation of alkylbenzenes and cyclo-alkylbenzenes. For example, supplementation of wild-type P450BM3 with 5-cyclohexylvaleric acid-L-phenylalanine (5CHVA-Phe) and Z-proline-L-phenylalanine yielded 53% (R) ee and 56% (S) ee for indane hydroxylation, respectively, although 16% (S) ee was still observed in the absence of any additives. Moreover, we performed a successful crystal structure analysis of 5CHVA-L-tryptophan-bound P450BM3 at 2.00 angstrom, which suggests that the changes in selectivity observed were caused by conformational changes in the enzyme induced by binding of the decoy molecules.
DOI： 10.1039/c7cy01130j
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Direct Hydroxylation of Benzene to Phenol by Cytochrome P450BM3 Triggered by Amino Acid Derivatives
Osami Shoji, Sota Yanagisawa, Joshua Kyle Stanfield, Kazuto Suzuki, Zhiqi Cong, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
Angewandte Chemie - International Edition Vol. 56 ( 35 ) page： 10324 - 10329 2017
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The selective hydroxylation of benzene to phenol, without the formation of side products resulting from overoxidation, is catalyzed by cytochrome P450BM3 with the assistance of amino acid derivatives as decoy molecules. The catalytic turnover rate and the total turnover number reached 259 min−1 P450BM3−1 and 40 200 P450BM3−1 when N-heptyl-l-proline modified with l-phenylalanine (C7-l-Pro-l-Phe) was used as the decoy molecule. This work shows that amino acid derivatives with a totally different structure from fatty acids can be used as decoy molecules for aromatic hydroxylation by wild-type P450BM3. This method for non-native substrate hydroxylation by wild-type P450BM3 has the potential to expand the utility of P450BM3 for biotransformations.
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A Substrate-Binding-State Mimic of H2O2-Dependent Cytochrome P450 Produced by One-point Mutagenesis and Peroxygenation of Non-native Substrates Reviewed
O. Shoji, T. Fujishiro, K. Nishio, Y. Kano, H. Kimoto, S. Chien, H. Onoda, A. Muramatsu, S. Tanaka, A. Hori, H. Sugimoto, Y. Shiro, Y. Watanabe
Catal. Sci. Tech. Vol. 6 page： 5806-5811 2016.8
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DOI： 10.1039/C6CY00630B
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Improved oxidation of aromatic and aliphatic hydrocarbons using rate enhancing variants of P450Bm3 in combination with decoy molecules Reviewed
S. D. Munday, O. Shoji, Y. Watanabe, L. L. Wong, S. G. Bell
Chem. Commun. Vol. 52 page： 1036-1039 2016.1
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Acetate anion-triggered peroxygenation of non-native substrates by wild-type cytochrome P450s Reviewed
H. Onoda, O. Shoji, Y. Watanabe
Dalton Trans Vol. 44 page： 15316-15323 2015.8
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DOI： 10.1039/C5DT00797F
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Highly efficient hydroxylation of gaseous alkanes at reduced temperature catalyzed by cytochrome P450BM3 assisted by decoy molecules Reviewed
N. Kawakami, Z. Cong, O. Shoji, Y. Watanabe
Journal of Porphyrins and Phthalocyanines Vol. 19 page： 329-334 2015.3
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Activation of Wild-type Cytochrome P450BM3 by the Next Generation of Decoy Molecules: Enhanced Hydroxylation of Gaseous Alkanes and Crystallographic Evidence Reviewed
Z. Cong, O. Shoji, C. Kasai, N. Kawakami, H. Sugimoto, Y. Shiro, Y. Watanabe
ACS Catalysis Vol. 5 page： 150–156 2015.1
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DOI： 10.1021/cs501592f
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Bringing out the potential of wild-type cytochrome P450s using decoy molecules: Oxygenation of nonnative substrates by bacterial cytochrome P450s Reviewed
O. Shoji, Y. Watanabe
Isr. J. Chem. Vol. 55 ( 1 ) page： 32–39 2015.1
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GluN2B-Selective N-Methyl-d-aspartate (NMDA) Receptor Antagonists Derived from 3-Benzazepines: Synthesis and Pharmacological Evaluation of Benzo[7]annulen-7-amines Reviewed
A. Benner, A. Bonifazi, C. Shirataki, L. Temme, D. Schepmann, W. Quaglia, O. Shoji, Y. Watanabe, C. Daniliuc, B. Wünsch
ChemMedChem Vol. 9 ( 4 ) page： 741-751 2014.4
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Inhibition of Heme Uptake in Pseudomonas aeruginosa by its Hemophore (HasAp) Bound to Synthetic Metal Complexes Reviewed
C. Shirataki, O. Shoji, M. Terada, S. Ozaki, H. Sugimoto, Y. Shiro, Y. Watanabe
Angew. Chem. Int. Ed. Vol. 53 page： 2862-2866 2014.3
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Peroxygenase reactions catalyzed by cytochromes P450 Reviewed
O. Shoji, Y. Watanabe
J. Biol. Inorg. Chem Vol. 19 ( 4-5 ) page： 529-539 2014.2
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Electronic Control of Discrimination between O2 and CO in Myoglobin Lacking the Distal Histidine Residue Reviewed
R. Nishimura, T. Shibata, I. Ishigami, T. Ogura, H. Tai, S. Nagao, T. Matsuo, S Hirota, O. Shoji, Y. Watanabe, K. Imai, S. Neya, A. Suzuki, Y. Yamamoto
Inorg. Chem Vol. 53 page： 1091–1099 2013.12
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Highly Selective Hydroxylation of Benzene to Phenol by Wild-type Cytochrome P450BM3 Assisted by Decoy Molecules Reviewed
O. Shoji, T. Kunimatsu, N. Kawakami, Y. Watanabe
Angew. Chem. Int. Ed. Vol. 52 page： 6606-6610 2013.6
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Direct hydroxylation of primary carbons in small alkanes by wild-type cytochrome P450BM3 containing perfluorocarboxylic acids as decoy molecules Reviewed
N. Kawakami, O. Shoji, Y. Watanabe
Chem. Sci. Vol. 4 page： 2344-2348 2013.3
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Chiral-Substrate-Assisted Stereoselective Epoxidation Catalyzed by H2O2-Dependent Cytochrome P450SPα Reviewed
T. Fujishiro, O. Shoji, N. Kawakami, T. Watanabe, H. Sugimoto, Y. Shiro, Y. Watanabe
Chemistry-An Asian Journal Vol. 7 ( 10 ) page： 2286-2293 2012.10
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Single-step reconstitution of apo-hemoproteins at the disruption stage of Escherichia coli cells Reviewed
N. Kawakami, O. Shoji, Y.Watanabe
ChemBioChem Vol. 13 ( 14 ) page： 2045-2047 2012.9
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Construction of Biocatalysts Using the Myoglobin Scaffold for the Synthesis of Indigo from Indole Reviewed
J. Xu, O. Shoji, T. Fujishiro, T. Ohki, T. Ueno, Y. Watanabe
Catalysis Science & Technology Vol. 2 page： 739-744 2012.4
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Molecular Design of Heme Proteins for Future Application Reviewed
H. Nakajima, O. Shoji, Y. Watanabe
Catalysis Surveys from Asia Vol. 15 ( 3 ) page： 134-143 2011.6
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This review surveys our recent studies on artificial heme oxygenases, which consists of two topics. The first topic is an artificial peroxidase founded on a thermally tolerant protein, which shows high thermal stability in the catalytic reaction. In the second topic, we describe `Decoy system' that has been developed to transform Cytochrome P450BSβ into a versatile oxygenase.
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Crystal structure of H2O2-dependent cytochrome P450SPα with its bound fatty acid substrate: insight into the regioselective hydroxylation of fatty acids at the α position Reviewed
T. Fujishiro, O. Shoji, S. Nagano, H. Sugimoto, Y. Shiro, Y. Watanabe
J. Biol. Chem. Vol. 286 page： 29941-29950 2011.6
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Use of Perfluoro Carboxylic Acids Trick Cytochrome P450BM3 into Initiating Hydroxylation of Gaseous Alkanes Reviewed
N. Kawakami, O. Shoji, Y. Watanabe
Angew.Chem.Int.Ed Vol. 50 page： 5315-5318 2011.4
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It has long been believed that the fatty acid hydroxylase wild-type P450BM3 is unable to oxidize gaseous alkanes. However, the simple addition of a perfluorocarboxylic acid as a dummy substrate to initiate the P450BM3 catalytic cycle enabled the efficient hydroxylation of butane and propane (see picture).
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Design of H2O2-Dependent Oxidation Catalyzed by Hemoproteins Reviewed
O. Shoji, Y. Watanabe
Metallomics Vol. 3 page： 379-388 2011.2
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The monooxygenese activity of cytochrome P450 is successfully introduced into myoglobin by rational design of its active site. Introduction of an aromatic ring, tryptophan, near the heme by site-directed mutagenesis resulted in the hydroxylation of tryptophan at the C6 position by using an almost stoichiometric amount of H(2)O(2). We also altered the substrate specificity of H(2)O(2)-dependent P450 by employing a simple substrate trick. Although P450(BSβ) exclusively catalyzes peroxygenation of long-alkyl-chain fatty acids, oxidation of non-natural substrates such as styrene, ethylbenzene, and 1-methoxynaphthalen are catalyzed by P450(BSβ) in the presence of decoy molecules having a carboxyl group. Advantageously, the substrate specificity of P450(BSβ) can be altered by simply adding the decoy molecule without replacing any amino acid residues. Moreover, the stereoselectivity can be controlled by changing the structure of the decoy molecule. The crystal structure analysis of the decoy molecule bound-form of P450(BSβ) shows that P450(BSβ) accepts the decoy molecule, whose carboxylate is located at the same position to that of long-alkyl-chain fatty acid.
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Non-covalent modification of the active site of cytochrome P450 for inverting the stereoselectivity of monooxygenation Reviewed
Takashi Fujishiro, Osami Shoji, Yoshihito Watanabe
Tetrahedron Letters Vol. 53 ( 3 ) page： 395-397 2010.12
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The enantioselectivity in the sulfoxidation of thioanisole catalyzed by cytochrome P450BSβ with a decoy molecule, a dummy molecule of the natural substrate, can be inverted by changing the structure of the decoy molecule. The methodology demonstrated herein shows the potential for controlling the stereoselectivity of biocatalysts without any mutagenesis.
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Understanding substrate misrecognition of hydrogen peroxide dependent cytochrome P450 from Bacillus subtilis Reviewed
Osami Shoji, Takashi Fujishiro, Shingo Nagano, Shota Tanaka, Takuya Hirose, Yoshitsugu Shiro, Yoshihito Watanabe
J. Biol. Inorg. Chem. Vol. 15 ( 8 ) page： 1331-1339 2010.8
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Cytochrome P450(BSβ), a H(2)O(2)-dependent cytochrome P450 catalyzing the hydroxylation of long-alkyl-chain fatty acids, lacks the general acid-base residue around the heme, which is indispensable for the efficient generation of the active species using H(2)O(2). On the basis of the crystal structure of the palmitic acid bound form of cytochrome P450(BSβ), it was suggested that the role of the general acid-base function was provided by the carboxylate group of fatty acids. The participation of the carboxylate group of the substrate was supported by the fact that cytochrome P450(BSβ) can catalyze oxidations of nonnatural substrates such as styrene and ethylbenzene in the presence of a series of short-alkyl-chain carboxylic acids as a dummy molecule of fatty acid. We refer to a series of short-alkyl-chain carboxylic acids as a "decoy molecule". As shown here, we have clarified the crystal structure of the decoy-molecule-bound form and elucidated that the location of its carboxylate group is virtually the same as that of palmitic acid in the heme cavity, indicating that the carboxylate group of the decoy molecule serves as the general acid-base catalyst. This result further confirms that the role of the acid-base function is satisfied by the carboxylate group of the substrates. In addition, the structure analysis of the substrate-free form has clarified that no remarkable structural change is induced by the binding of the decoy molecule as well as fatty acid. Consequently, whether the carboxylate group is positioned in the active site provides the switching mechanism of the catalytic cycle of cytochrome P450(BSβ).
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Aromatic C-H bond hydroxylation by P450 peroxygenases: a facile colorimetric assay for monooxygenation activities of enzymes based on Russig's blue formation Reviewed
Osami Shoji, Christian Wiese, Takashi Fujishiro, Chikako Shirataki, Bernhard Wünsch, Yoshihito Watanabe
J. Biol. Inorg. Chem. Vol. 15 ( 7 ) page： 1109-1115 2010.5
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Aromatic C-H bond hydroxylation of 1-methoxynaphthalene was efficiently catalyzed by the substrate misrecognition system of the hydrogen peroxide dependent cytochrome P450BSβ (CYP152A1), which usually catalyzes hydroxylation of long-alkyl-chain fatty acids. Very importantly, the hydroxylation of 1-methoxynaphthalene can be monitored by a color change since the formation of 4-methoxy-1-naphthol was immediately followed by its further oxidation to yield Russig's blue. Russig's blue formation allows us to estimate the peroxygenation activity of enzymes without the use of high performance liquid chromatography, gas chromatography, and nuclear magnetic resonance measurements.
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Hydrogen Peroxide-Dependent Monooxygenations by Tricking the Substrate Recognition of Cytochrome P450BSb Reviewed
Osami Shoji, Takashi Fujishiro, Hiroshi Nakajima, Misa Kim, Shingo Nagano, Yoshitsugu Shiro, Yoshihito Watanabe
Angew. Chem. Int. Ed. Vol. 46 ( 20 ) page： 3656-3659 2007.5
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Supramolecular array of imizazolylethynyl-zinc-porphyrin Reviewed
Akiharu Satake, Osami Shoji, Yoshiaki Kobuke
J. Organomet. Chem. Vol. 692 ( 1-3 ) page： 635-644 2006.8
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Single Molecule Visualization of Coordination Assembled Porphyrin Macrocycles Reinforced with Covalent Linkings Reviewed
Osami Shoji, Hiroyuki Tanaka, Tomoji Kawai, Yoshiaki Kobuke
J. Am. Chem. Soc Vol. 127 ( 24 ) page： 8598 -8599 2005.5
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Coordination Assembled Rings of Ferrocene-Bridged Trisporphyrin with Flexible Hinge-like Motion: Selective Dimer Ring Formation, its Transformation to Larger Rings, and Vice Versa Reviewed
Osami Shoji, Saori Okada, Akiharu Satake, Yoshiaki Kobuke
J. Am. Chem. Soc Vol. 127 ( 7 ) page： 2201-2210 2005.2
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Temperature Dependence of Circular Dichroism and Fluorescence Decay of Pyrene Appended to the Side Chains of Poly-L-glutamine Reviewed
Osami Shoji, Daisuke Nakajima, Masahiro Ohkawa, Yoshiki Fujiwara, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira
Macromolecules Vol. 36 ( 12 ) page： 4557-4566 2003.5
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Side-chain Chromophore Orientation and Excitation Energy Transport in Films Prepared from Poly[N5-(R)- and N5-(S)-1-(1-naphthyl)ethyl-L-glutamines] Reviewed
Osami Shoji, Yachiyo Higashi, Sachie Hishinuma, Masaki Sato, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira
Macromolecules Vol. 35 ( 6 ) page： 2116-2121 2002.2
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Highly controlled side-chain chromophore orientation in poly[N5-1-(1-pyrenyl)ethyl--glutamines] Reviewed
Osami Shoji, Daisuke Nakajima, Masahiko Annaka, Masako Yoshikuni, Takayuki Nakahira
Polymer Vol. 43 ( 5 ) page： 1711-1714 2001.11
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Poly[N5-(R and S)-1-(1-pyrenyl)ethyl-Image -glutamines] (1 and 2) were prepared by condensation of poly(Image -glutamic acid) with optically resolved amines. In solution, these polymers, 2 in particular, gave large circular dichroism (CD) indicative of exciton coupling among the side-chain pyrene chromophores. When compared with the corresponding polymer with achiral side groups, i.e. poly(1-pyrenylmethyl-Image -glutamine) (3), 1 and 2 not only gave much stronger CD, but also gave much reduced excimer emission with a significant hypsochromic shift of emission maximum. The highly controlled orientation of the side-chain chromophores is apparently brought about by the specific steric interactions among the bulky chiral side chains along the helical main chain.
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Secondary Structure and Side-Chain Chromophore Orientation in Poly(L-glutamines) Having Pyrene Chromophores in the Side Chains Reviewed
Osami Shoji, Masataka Okumura, Hiromi Kuwata, Takuma Sumida, Ryo Kato, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira
Macromolecules Vol. 34 ( 12 ) page： 4270-4276 2001.5
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Books
Books 20
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酵素機能を化学的にハックする新規手法の開発、触媒年鑑：触媒技術の動向と展望 2021年版
大村慧太, 愛場 雄一郎, 有安 真也, 荘司 長三（ Role： Joint author）
一般社団法人触媒学会 2021
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ペプチド核酸と相分離, 相分離生物学の全貌, 現代化学 増刊
愛場 雄一郎, 荘司 長三（ Role： Sole author）
現代化学 2020
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Language：Japanese
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人工金属タンパク質で緑膿菌を狙い撃ち 緑膿菌が分泌するヘムタンパク質で金属フタロシアニンを送り込む
荘司長三、四坂勇磨（ Role： Joint author）
ファルマシア（日本薬学会会報誌） 2020
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Language：Japanese
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感染症「鉄の取り込みを阻害する新しい抗菌薬の開発」
四坂勇磨、荘司長三（ Role： Joint author）
アステラス製薬株式会社 2018.9
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感染症「鉄の取り込みを阻害する新しい抗菌薬の開発」
四坂勇磨, 荘司長三（ Role： Joint author）
アステラス製薬株式会社 2018.9
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Responsible for pages：18-21 Language：Japanese
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化学と生物「擬似基質による酵素活性化と高難度酸化反応」
荘司長三（ Role： Joint author）
公益社団法人日本農芸化学会 2018.8
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化学と生物「擬似基質による酵素活性化と高難度酸化反応」
荘司長三（ Role： Joint author）
公益社団法人日本農芸化学会 2018.8
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Responsible for pages：621-626 Language：Japanese
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石油学会ペトロテック「酸化酵素の誤作動を利用するバイオ触媒開発」
荘司長三（ Role： Sole author）
公益社団法人石油学会 2018.5
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石油学会ペトロテック「酸化酵素の誤作動を利用するバイオ触媒開発」
荘司長三（ Role： Sole author）
公益社団法人石油学会 2018.5
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Responsible for pages：390-394 Language：Japanese
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金属酵素による酸化反応と反応機構
荘司長三（ Role： Sole author）
㈱化学同人 『活性酸素・フリーラジカルの科学』日本化学会編 2016.3
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緑膿菌の増殖を阻害する「人工金属タンパク質」
荘司長三（ Role： Sole author）
公益社団法人日本化学会「化学と工業」 2015.2
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Monooxygenation of Small Hydrocarbons Catalyzed by Bacterial Cytochrome P450s
Osami Shoji, Yoshihito Watanabe（ Role： Joint author）
Springer 2015 （ ISBN:978-3-319-16008-5 ）
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「頑固な酵素」を巧みに騙す
荘司長三、渡辺芳人（ Role： Joint author）
生物工学会誌 2014.8
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Oxygenation of Nonnative Substrates Using a Malfunction State of Cytochrome P450s
O. Shoji, Y. Watanabe（ Role： Joint author）
Springer 2014.5
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化学掲示板 新聞に載った注目記事（2月） 2月5日 日本経済新聞 院内感染の原因菌, 緑膿菌の増殖を抑える技術を開発
荘司長三、白瀧千夏子（ Role： Joint author）
株式会社 化学同人 月刊「化学」 2014.3
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ベンゼンをフェノールに一段階で変換する新規バイオ触媒の開発
荘司長三、渡辺芳人（ Role： Joint author）
日本工業出版株式会社「配管技術」 2013.12
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酵素の基質誤認識を利用する不活性炭化水素の水酸化
荘司長三（ Role： Sole author）
公益社団法人日本化学会「化学と工業」 2013.9
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酵素を“誤作動”させて行う有機合成―― 酵素反応を有機化学に利用するための反応制御
荘司長三、渡辺芳人（ Role： Joint author）
株式会社 化学同人 月刊「化学」 2013.8
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P450による酸素活性化機構と基質の酸素化機構 "P450の分子生物学 第２版"
渡辺芳人、荘司長三（ Role： Joint author）
株式会社 講談社サイエンティフィック 2009.8
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注目の最新シトクロムP450の基礎と応用
解毒作用の主役P450の最新構造解析や、急発展した医学分野での研究を踏まえた改訂版。薬物代謝分野はもちろん、動植物、微生物などでの多彩な働きを紹介 -
酵素工学ニュース「ヘム酵素の創成」
渡辺芳人、荘司長三（ Role： Joint author）
酵素工学研究会誌 2009
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MISC
MISC 23
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Hitoki Nanaura, Honoka Kawamukai, Ayano Fujiwara, Takeru Uehara, Mari Nakanishi, Tomo Shiota, Masaki Hibino, Yuichiro Aiba, Pattama Wiriyasermkul, Sotaro Kikuchi, Riko Nagata, Masaya Matsubayashi, Shushi Nagamori, Osami Shoji, Koichiro Ishimori, Hiroyoshi Matsumura, Kazuma Sugie, Tomohide Saio, Takuya Yoshizawa, Eiichiro Mori
2019.10
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Publisher：Cold Spring Harbor Laboratory
<title>ABSTRACT</title>Low-complexity (LC) domains of proteins are found in about one fifth of human proteome, and a group of LC-domains form labile cross-β polymers and liquid-like droplets. Polymers and droplets formed from LC-domains are dynamically regulated by posttranslational modifications and molecular chaperones including nuclear transport receptors. Repeat expansion in the first intron of a gene designated <italic>C9orf72</italic>, which is the most prevalent form of familial amyotrophic lateral sclerosis (ALS), causes nucleocytoplasmic transport deficit, however, the detailed mechanism remains unsolved. Here we show that the proline:arginine (PR) poly-dipeptides encoded by the <italic>C9orf72</italic> repeat expansion bound nuclear transport receptor Kapβ2 through its nuclear localization signal (NLS) recognition motif, and inhibited the ability of Kapβ2 to melt fused in sarcoma (FUS) droplets by competing interaction with FUS. The findings in this study offer mechanistic insights as to how the <italic>C9orf72</italic> repeat expansion disables nucleocytoplasmic transport and causes neurodegenerative diseases.
DOI： 10.1101/812099
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Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives
Masayuki Karasawa, Joshua Kyle Stanfield, Sota Yanagisawa, Osami Shoji, Yoshihito Watanabe
Angewandte Chemie International Edition Vol. 57 ( 38 ) page： 12264 - 12269 2018.9
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Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives Reviewed
M. Karasawa, J. K. Stanfield, S. Yanagisawa, O. Shoji, Y. Watanabe
Angew. Chem. Int. Ed. Vol. 57 page： 12264-12269 2018.9
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Peptide Nucleic Acid Conjugated with Ru-complex Stabilizing Double-Duplex Invasion Complex Even under Physiological Conditions Reviewed
M. Hibino, Y. Aiba, Y. Watanabe, O. Shoji
ChemBioChem Vol. 19 page： 1601-1604 2018.8
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Cover Feature: Peptide Nucleic Acid Conjugated with Ruthenium-Complex Stabilizing Double-Duplex Invasion Complex Even under Physiological Conditions (ChemBioChem 15/2018) Reviewed
Masaki Hibino, Yuichiro Aiba, Yoshihito Watanabe, Osami Shoji
ChemBioChem Vol. 19 ( 15 ) page： 1601-1604 2018.8
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Metabolic enhancement of 2,3 ',4,4 ',5-pentachlorobiphenyl (CB118) using cytochrome P450 monooxygenase isolated from soil bacterium under the presence of perfluorocarboxylic acids (PFCAs) and the structural basis of its metabolism International journal
Goto Erika, Haga Yuki, Kubo Makoto, Itoh Toshimasa, Kasai Chie, Shoji Osami, Yamamoto Keiko, Matsumura Chisato, Nakano Takeshi, Inui Hideyuki
CHEMOSPHERE Vol. 210 page： 376-383 - 383 2018.7
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2,3',4,4',5-Pentachlorobiphenyl (CB118) is one of the most abundant polychlorinated biphenyl (PCB) congeners in the environment, and perfluoroalkyl acids, including perfluorocarboxylic acids (PFCAs), are widely distributed in the environment. Although CB118 and perfluoroalkyl acids are present in all humans and biota, effects in the metabolic fate of CB118 leading to toxicity change are unclear. P450BM3, which is isolated from the soil bacterium Bacillus megaterium, metabolized CB118 to three different hydroxylated pentachlorobiphenyls (M1-M3). M2 was identified as 4'-OH-2,3',4,5,5'-pentachlorobiphenyl. These reactions were promoted by the presence of PFCAs, and perfluorooctanoic acid (PFCA-C8) was the most effective for accelerating these reactions among PFCAs with different carbon chain length. The production rate of M2 was accelerated by 25-times using PFCA-C8. Furthermore, the docking models of P450BM3 with CB118 and PFCAs revealed that the conformational changes of the substrate-binding cavity of P450BM3 after binding of PFCAs to P450BM3 were important for selective production of CB118 metabolites. This study leads to the clarification of the different metabolic fates of PCBs under complex contamination with PFCAs.
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Metabolic enhancement of 2,3´,4,4´,5-pentachlorobiphenyl (CB118) using cytochrome P450 monooxygenase isolated from soil bacterium under the presence of perfluorocarboxylic acids (PFCAs) and the structural basis of its metabolism Reviewed International journal
E. Goto, Y. Haga, M. Kubo, T. Itoh, C. Kasai, O. Shoji, K. Yamamoto, C. Matsumura, T. Nakano, H. Inui
Chemosphere Vol. 210 page： 376-383 - 383 2018.7
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal)
2,3',4,4',5-Pentachlorobiphenyl (CB118) is one of the most abundant polychlorinated biphenyl (PCB) congeners in the environment, and perfluoroalkyl acids, including perfluorocarboxylic acids (PFCAs), are widely distributed in the environment. Although CB118 and perfluoroalkyl acids are present in all humans and biota, effects in the metabolic fate of CB118 leading to toxicity change are unclear. P450BM3, which is isolated from the soil bacterium Bacillus megaterium, metabolized CB118 to three different hydroxylated pentachlorobiphenyls (M1-M3). M2 was identified as 4'-OH-2,3',4,5,5'-pentachlorobiphenyl. These reactions were promoted by the presence of PFCAs, and perfluorooctanoic acid (PFCA-C8) was the most effective for accelerating these reactions among PFCAs with different carbon chain length. The production rate of M2 was accelerated by 25-times using PFCA-C8. Furthermore, the docking models of P450BM3 with CB118 and PFCAs revealed that the conformational changes of the substrate-binding cavity of P450BM3 after binding of PFCAs to P450BM3 were important for selective production of CB118 metabolites. This study leads to the clarification of the different metabolic fates of PCBs under complex contamination with PFCAs.
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Dual-Functional Small Molecules for Generating an Efficient Cytochrome P450BM3 Peroxygenase
Nana Ma, Zhifeng Chen, Jie Chen, Jingfei Chen, Cong Wang, Haifeng Zhou, Lishan Yao, Osami Shoji, Yoshihito Watanabe, Zhiqi Cong
Angewandte Chemie - International Edition Vol. 57 ( 26 ) page： 7628 - 7633 2018.6
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：Wiley-VCH Verlag
We report a unique strategy for the development of a H2O2-dependent cytochrome P450BM3 system, which catalyzes the monooxygenation of non-native substrates with the assistance of dual-functional small molecules (DFSMs), such as N-(ω-imidazolyl fatty acyl)-l-amino acids. The acyl amino acid group of DFSM is responsible for bounding to enzyme as an anchoring group, while the imidazolyl group plays the role of general acid–base catalyst in the activation of H2O2. This system affords the best peroxygenase activity for the epoxidation of styrene, sulfoxidation of thioanisole, and hydroxylation of ethylbenzene among those P450–H2O2 system previously reported. This work provides the first example of the activation of the normally H2O2-inert P450s through the introduction of an exogenous small molecule. This approach improves the potential use of P450s in organic synthesis as it avoids the expensive consumption of the reduced nicotinamide cofactor NAD(P)H and its dependent electron transport system. This introduces a promising approach for exploiting enzyme activity and function based on direct chemical intervention in the catalytic process.
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Dual-Functional Small Molecules for Generating an Efficient Cytochrome P450BM3 Peroxygenase Reviewed
Nana Ma, Zhifeng Chen, Jie Chen, Jingfei Chen, Cong Wang, Haifeng Zhou, Lishan Yao, Osami Shoji, Yoshihito Watanabe, Zhiqi Cong
Angewandte Chemie - International Edition Vol. 57 ( 26 ) page： 7628 - 7633 2018.6
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：Wiley-VCH Verlag
We report a unique strategy for the development of a H2O2-dependent cytochrome P450BM3 system, which catalyzes the monooxygenation of non-native substrates with the assistance of dual-functional small molecules (DFSMs), such as N-(ω-imidazolyl fatty acyl)-l-amino acids. The acyl amino acid group of DFSM is responsible for bounding to enzyme as an anchoring group, while the imidazolyl group plays the role of general acid–base catalyst in the activation of H2O2. This system affords the best peroxygenase activity for the epoxidation of styrene, sulfoxidation of thioanisole, and hydroxylation of ethylbenzene among those P450–H2O2 system previously reported. This work provides the first example of the activation of the normally H2O2-inert P450s through the introduction of an exogenous small molecule. This approach improves the potential use of P450s in organic synthesis as it avoids the expensive consumption of the reduced nicotinamide cofactor NAD(P)H and its dependent electron transport system. This introduces a promising approach for exploiting enzyme activity and function based on direct chemical intervention in the catalytic process.
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Reconstitution of Full-Length P450BM3 with an Artificial Metal Complex by Utilising the Transpeptidase Sortase A Reviewed
K. Omura, Y. Aiba, H. Onoda, J. K. Stanfield, S. Ariyasu, H. Sugimoto, Y. Shiro, O. Shoji, Y. Watanabe
Chem. Commun. Vol. 54 page： 7892-7895 2018.5
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DOI： 10.1039/C8CC02760A
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Reconstitution of full-length P450BM3 with an artificial metal complex by utilising the transpeptidase Sortase A Reviewed
Omura Keita, Aiba Yuichiro, Onoda Hiroki, Stanfield Joshua Kyle, Ariyasu Shinya, Sugimoto Hiroshi, Shiro Yoshitsugu, Shoji Osami, Watanabe Yoshihito
CHEMICAL COMMUNICATIONS Vol. 54 ( 57 ) page： 7892-7895 2018.5
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DOI： 10.1039/c8cc02760a
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Hydroxylation of gaseous alkanes and benzene catalyzed by cytochrome P450BM3 using decoy molecules as a substrate analogue
Shoji Osami, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Switchable stereoselectivity in monooxygenation of non-native substrates by P450BM3 using decoy molecules
Suzuki Kazuto, Shoji Osami, Stanfield Joshua, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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Reconstitution of self-sufficient cytochrome P450 with artificial metal complexes
Omura Keita, Aiba Yuichiro, Ariyasu Shinya, Shoji Osami, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol. 255 page： . 2018.3
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α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids Reviewed
H. Onoda, O.Shoji, K.Suzuki, H.Sugimoto, Y.Shiro, Y.Watanabe
Catal. Sci. Technol. Vol. 8 ( 2 ) page： 434-442 2018.2
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DOI： 10.1039/C7CY02263H
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α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids
Hiroki Onoda, Osami Shoji, Kazuto Suzuki, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
Catalysis Science and Technology Vol. 8 ( 2 ) page： 434 - 442 2018
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：Royal Society of Chemistry
Cytochrome P450 peroxygenases belonging to the CYP152 family catalyse the oxidation of fatty acids using H2O2. CYP152N1 isolated from Exiguobacterium sp. AT1b exclusively catalyses the α-selective hydroxylation of myristic acid at physiological H2O2 concentration. However, a series of shorter-alkyl-chain fatty acids such as tridecanoic acid were produced from myristic acid by increasing the concentration of H2O2 (1-10 mM). The yield of tridecanoic acid from myristic acid reached 17%. An 18O-labeled oxidant study suggested that CYP152N1 catalysed the overoxidation of α-hydroxymyristic acid to form α-ketomyristic acid, which in turn was spontaneously decomposed by H2O2 to yield tridecanoic acid. Crystal structure analysis of CYP152N1 revealed its high similarity to other CYP152 family enzymes, such as CYP152A1 and CYP152B1. MD simulations of α-hydroxymyristic acid accommodated in CYP152N1 proposed a possible pre-oxidation conformation of α-hydroxymyristic acid for the decarboxylation reaction.
DOI： 10.1039/c7cy02263h
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Inside Back Cover: Structures of the Heme Acquisition Protein HasA with Iron(III)-5,15-Diphenylporphyrin and Derivatives Thereof as an Artificial Prosthetic Group (Angew. Chem. Int. Ed. 48/2017)
Hiromu Uehara, Yuma Shisaka, Tsubasa Nishimura, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihiro Miyake, Hiroshi Shinokubo, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie International Edition Vol. 56 ( 48 ) page： 15471 - 15471 2017.11
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Structures of the Heme Acquisition Protein HasA with Iron(III)-5,15-Diphenylporphyrin and Derivatives Thereof as an Artificial Prosthetic Group Reviewed
Hiromu Uehara, Yuma Shisaka, Tsubasa Nishimura, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihiro Miyake, Hiroshi Shinokubo, Yoshihito Watanabe, Osami Shoji
Angewandte Chemie Vol. 129 ( 48 ) page： 15481 - 15485 2017.11
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Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules Reviewed
Kazuto Suzuki, Joshua Kyle Stanfield, Osami Shoji, Sota Yanagisawa, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
CATALYSIS SCIENCE & TECHNOLOGY Vol. 7 ( 15 ) page： 3332 - 3338 2017.8
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：ROYAL SOC CHEMISTRY
The hydroxylation of non-native substrates catalysed by wild-type P450BM3 is reported, wherein "decoy molecules", i.e., native substrate mimics, controlled the stereoselectivity of hydroxylation reactions. We employed decoy molecules with diverse structures, resulting in either a significant improvement in enantio-selectivity or clear inversion of stereoselectivity in the benzylic hydroxylation of alkylbenzenes and cyclo-alkylbenzenes. For example, supplementation of wild-type P450BM3 with 5-cyclohexylvaleric acid-L-phenylalanine (5CHVA-Phe) and Z-proline-L-phenylalanine yielded 53% (R) ee and 56% (S) ee for indane hydroxylation, respectively, although 16% (S) ee was still observed in the absence of any additives. Moreover, we performed a successful crystal structure analysis of 5CHVA-L-tryptophan-bound P450BM3 at 2.00 angstrom, which suggests that the changes in selectivity observed were caused by conformational changes in the enzyme induced by binding of the decoy molecules.
DOI： 10.1039/c7cy01130j
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Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules
Kazuto Suzuki, Joshua Kyle Stanfield, Osami Shoji, Sota Yanagisawa, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
CATALYSIS SCIENCE & TECHNOLOGY Vol. 7 ( 15 ) page： 3332 - 3338 2017.8
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：ROYAL SOC CHEMISTRY
The hydroxylation of non-native substrates catalysed by wild-type P450BM3 is reported, wherein "decoy molecules", i.e., native substrate mimics, controlled the stereoselectivity of hydroxylation reactions. We employed decoy molecules with diverse structures, resulting in either a significant improvement in enantio-selectivity or clear inversion of stereoselectivity in the benzylic hydroxylation of alkylbenzenes and cyclo-alkylbenzenes. For example, supplementation of wild-type P450BM3 with 5-cyclohexylvaleric acid-L-phenylalanine (5CHVA-Phe) and Z-proline-L-phenylalanine yielded 53% (R) ee and 56% (S) ee for indane hydroxylation, respectively, although 16% (S) ee was still observed in the absence of any additives. Moreover, we performed a successful crystal structure analysis of 5CHVA-L-tryptophan-bound P450BM3 at 2.00 angstrom, which suggests that the changes in selectivity observed were caused by conformational changes in the enzyme induced by binding of the decoy molecules.
DOI： 10.1039/c7cy01130j
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Use of apomyoglobin to gently remove heme from a H2O2-dependent cytochrome P450 and allow its reconstitution
Shih-Cheng Chien, Osami Shoji, Yoshiko Morimoto, Yoshihito Watanabe
NEW JOURNAL OF CHEMISTRY Vol. 41 ( 1 ) page： 302 - 307 2017.1
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：ROYAL SOC CHEMISTRY
The heme of hydrogen peroxide-dependent cytochrome P450(BS beta) (P450(BS beta)) was removed by apomyoglobin under mild conditions to give apo-P450(BS beta) without the need for acidic conditions and organic solvents. The circular dichroism spectrum of the apo-P450(BS beta) was essentially identical to that of holo-P450(BS beta), showing a small structural change resulting from the removal of heme using apomyoglobin. The apo-P450(BS beta) was reconstituted with hemin or manganese protoporphyrin IX (MnPPIX), and the resulting reconstituted P450(BS beta) catalyzed the one-electron oxidation of guaiacol using hydrogen peroxide as an oxidant. A higher catalytic activity was observed for P450(BS beta) reconstituted with MnPPIX when meta-chloroperoxybenzoic acid (mCPBA) was used as the oxidant.
DOI： 10.1039/c6nj02882a
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Direct Hydroxylation of Benzene to Phenol by Cytochrome P450BM3 Triggered by Amino Acid Derivatives
Osami Shoji, Sota Yanagisawa, Joshua Kyle Stanfield, Kazuto Suzuki, Zhiqi Cong, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
Angewandte Chemie - International Edition Vol. 56 ( 35 ) page： 10324 - 10329 2017
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：Wiley-VCH Verlag
The selective hydroxylation of benzene to phenol, without the formation of side products resulting from overoxidation, is catalyzed by cytochrome P450BM3 with the assistance of amino acid derivatives as decoy molecules. The catalytic turnover rate and the total turnover number reached 259 min−1 P450BM3−1 and 40 200 P450BM3−1 when N-heptyl-l-proline modified with l-phenylalanine (C7-l-Pro-l-Phe) was used as the decoy molecule. This work shows that amino acid derivatives with a totally different structure from fatty acids can be used as decoy molecules for aromatic hydroxylation by wild-type P450BM3. This method for non-native substrate hydroxylation by wild-type P450BM3 has the potential to expand the utility of P450BM3 for biotransformations.
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Direct Hydroxylation of Benzene to Phenol by Cytochrome P450BM3 Triggered by Amino Acid Derivatives Reviewed
Osami Shoji, Sota Yanagisawa, Joshua Kyle Stanfield, Kazuto Suzuki, Zhiqi Cong, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
Angewandte Chemie - International Edition Vol. 56 ( 35 ) page： 10324 - 10329 2017
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Language：English Publishing type：Rapid communication, short report, research note, etc. (scientific journal) Publisher：Wiley-VCH Verlag
The selective hydroxylation of benzene to phenol, without the formation of side products resulting from overoxidation, is catalyzed by cytochrome P450BM3 with the assistance of amino acid derivatives as decoy molecules. The catalytic turnover rate and the total turnover number reached 259 min−1 P450BM3−1 and 40 200 P450BM3−1 when N-heptyl-l-proline modified with l-phenylalanine (C7-l-Pro-l-Phe) was used as the decoy molecule. This work shows that amino acid derivatives with a totally different structure from fatty acids can be used as decoy molecules for aromatic hydroxylation by wild-type P450BM3. This method for non-native substrate hydroxylation by wild-type P450BM3 has the potential to expand the utility of P450BM3 for biotransformations.
Presentations
Presentations 172
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Exploiting Decoy Molecule Invited International conference
O. Shoji
International Conference on Porphyrins and Phthalocyanines (ICPP) 2021.6.28
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Event date： 2021.6 - 2021.7
Language：English Presentation type：Oral presentation (invited, special)
Venue：Online
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金属酵素の誤作動誘起と高難度物質変換 Invited
荘司長三
第33回万有札幌シンポジウム 2021.6.26
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Event date： 2021.6
Presentation type：Oral presentation (invited, special)
Venue：オンライン
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金属酵素を誤作動させてメタンを水酸化する反応系の開発
荘司長三
2021年度CREST「革新的触媒」領域公開シンポジウム 2021.6.23
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Event date： 2021.6
Presentation type：Oral presentation (general)
Venue：オンライン
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シトクロムP450を誤作動させる分子を用いる高難度酸化反応
荘司 長三, 愛場 雄一郎, 有安 真也
日本農芸化学会大会2021 2021.3.21
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Event date： 2021.3
Language：Japanese Presentation type：Oral presentation (invited, special)
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金属酵素の誤作動誘起と高難度酸化反応 Invited
荘司長三
第53回酸化反応討論会
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Event date： 2020.11
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン Country：Japan
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金属酵素の誤作動誘起と高難度酸化反応 Invited
荘司 長三
第53回酸化反応討論会 2020.11.8
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Event date： 2020.11
Language：Japanese Presentation type：Oral presentation (keynote)
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緑膿菌の鉄獲得系を利用する選択的な光増感剤輸送と光殺菌 Invited
荘司長三
第94回日本感染症学会総会・学術講演会
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Event date： 2020.8
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：オンライン Country：Japan
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緑膿菌の鉄獲得系を利用する選択的な光増感剤輸送と光殺菌 Invited
荘司 長三
第94回日本感染症学会総会・学術講演会 2020.8.19
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Event date： 2020.8
Language：Japanese Presentation type：Oral presentation (invited, special)
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酵素を誤作動させる分子を使う物質変換 Invited
荘司 長三
第六回ケムステバーチャルシンポジウム「高機能性金属錯体が拓く触媒科学」 2020.7.29
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Event date： 2020.7
Language：Japanese Presentation type：Oral presentation (invited, special)
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Hydroxylation of nonnative substrates catalyzed by cytochrome P450BM3 exploiting decoy molecules International conference
O. Shoji
The 3rd IRCCS - The 2nd Reaction Infography Joint International Symposium: “Reaction Imaging Meets Materials Science"
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Event date： 2020.1 - 2020.2
Language：English Presentation type：Oral presentation (general)
Venue：Nagoya University Country：Japan
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酵素を欺く化学分子は役に立つか
荘司長三
第6回名古屋大学の卓越・先端・次世代研究シンポジウム「専門性と学際性の狭間で」
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Event date： 2020.1
Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Country：Japan
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Material Transformation Using Biocatalysts Assisted by External Additives International conference
O. Shoji
4th International Symposium on Precisely Designed Catalysts with Customized Scaffolding
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Event date： 2019.12
Language：English Presentation type：Oral presentation (general)
Venue：Nara, Japan Country：Japan
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Exploiting Decoy Molecules International conference
Osami Shoji
2019 Korea-Taiwan-Japan Bioinorganic Chemistry Symposium
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Event date： 2019.11
Language：English Presentation type：Oral presentation (general)
Venue：Taichung City, Taiwan Country：Taiwan, Province of China
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HYDROXYLATION OF NONNATIVE SUBSTRATES BY CYTOCHROME P450BM3 EXPLOITING DECOY MOLECULES Invited International conference
Osami Shoji
12th China Japan Joint Symposium on Metal Cluster Compounds (CJJSMCC2019)
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Event date： 2019.10
Language：English Presentation type：Symposium, workshop panel (nominated)
Venue：Taichung City, Taiwan Country：China
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"Hydroxylation of Nonnative Substrates by Cytochrome P450BM3 Exploiting Decoy Molecules
O.Shoji
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Event date： 2019.9
Language：English Presentation type：Symposium, workshop panel (nominated)
Country：Japan
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Use of Decoy Molecules to Trick Cytochrome P450s
O.Shoji
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Event date： 2019.9
Language：English Presentation type：Symposium, workshop panel (nominated)
Country：Japan
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Hydroxylation of Nonnative Substrates by Cytochrome P450BM3 Exploiting Decoy Molecules International conference
Osami Shoji
19th International Conference on Biological Inorganic Chemistry (ICBIC-19)
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Event date： 2019.8
Language：English Presentation type：Oral presentation (general)
Venue： Interlaken Country：Switzerland
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Whole-Cell Biotransformation Catalysed by Intracellular Cytochrome P450BM3 Activated by Decoy Molecules Invited International conference
Osami Shoji
ArtZymes 2.0
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Event date： 2019.8
Language：English Presentation type：Oral presentation (invited, special)
Venue：Basel Country：Switzerland
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酵素の誤作動を誘起する分子の開発と物質変換 Invited
荘司長三
日本化学会東北支部山形地区講演会—生体外で活躍するタンパク質—
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Event date： 2019.7
Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：山形市 Country：Japan
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シトクロムP450の基質誤認識を利用する菌体内物質変換 Invited
荘司長三
第19回日本蛋白質科学会年会第71回日本細胞生物学会大会合同年次大会
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Event date： 2019.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：兵庫 Country：Japan
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Use of Decoy Molecules to Trick Cytochrome P450BM3 into Hydroxylating Nonnative Substrates International conference
Osami Shoji
the 21st International Conference on Cytochrome P450
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Event date： 2019.6
Language：English Presentation type：Oral presentation (general)
Venue：Brisbane Country：Australia
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Assisted by Decoy Molecules Invited International conference
Osami Shoji
15th International Symposium on Applied Bioinorganic Chemistry (ISABC15)
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Event date： 2019.6
Language：English Presentation type：Oral presentation (keynote)
Venue：Nara Country：Japan
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Cheating Cytochrome P450BM3 into Hydroxylating Non-Native Substrates by Exploiting its Substrate Misrecognition Invited
O. Shoji
Let's leap! Challenges in Organic Chemistry
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Event date： 2019.4
Language：English Presentation type：Public lecture, seminar, tutorial, course, or other speech
Country：Japan
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Facilitated by Decoy Molecules Invited
Osami Shoji
New Frontier in Protein Design & Engineering
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Event date： 2019.3
Language：English Presentation type：Symposium, workshop panel (nominated)
Country：Japan
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酸化酵素の誤作動を誘起する低分子化合物による基質特異性変換 Invited
荘司長三
日本におけるケミカルバイオロジーの新展開第189委員会 平成30年度 第4回定例会
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Event date： 2019.3
Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：大阪市 Country：Japan
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酸化酵素の誤作動を誘起する擬似基質を用いる物質変換 Invited
荘司長三
分子研研究会「錯体化学を基盤とした階層構造制御と機能発現」
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Event date： 2019.3
Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：愛知 Country：Japan
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 Activated by External Additives Invited
Osami Shoji
Core-to-Core Symposium Elements Function for Transformative Catalysis and Materials
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Event date： 2019.2
Language：English Presentation type：Symposium, workshop panel (nominated)
Country：Japan
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金属蛋白質の対象誤認識を利用する機能改変 Invited
荘司長三
新学術領域研究「高難度物質変換反応の開発を指向した精密制御反応場の創出」第６回公開シンポジウム
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Event date： 2019.1
Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：京都 Country：Japan
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 with Decoy Moleculues Invited International conference
O.Shoji
2nd China-Japan Joint Symposium on the Biosynthesis of Natural Products
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Event date： 2019.1
Language：English Presentation type：Oral presentation (invited, special)
Venue： Guangzhou, China Country：China
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金属酵素の誤作動を利用する物質変換 Invited
荘司長三
新学術「生合成リデザイン」第５回公開シンポジウム
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Event date： 2018.12
Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：千葉 Country：Japan
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Hydroxylation of Nonnative Substrates Catalyzed by Wild-type Cytochrome P450BM3 with Decoy Molecules Invited International conference
O.Shoji
The 13th International Symposium on Organic Reactions
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Event date： 2018.11
Language：English Presentation type：Oral presentation (invited, special)
Venue：Hsinchu, Taiwan Country：Taiwan, Province of China
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酸化酵素の誤作動を利用する物質変換 Invited
荘司長三
酵素工学研究会第80回講演会
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Event date： 2018.11
Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京 Country：Japan
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ベンゼンをフェノールに変換するバイオ触媒系の開発
荘司長三
第49回中部化学関係学協会支部連合秋季大会
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Event date： 2018.11
Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：名古屋 Country：Japan
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 Facilitated by Decoy Moleculues International conference
O.Shoji
FHI-JST Joint Symposium,Current Topics and Challenges for Innovative Catalysts
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Event date： 2018.10 - 2018.11
Language：English Presentation type：Oral presentation (general)
Venue：Berlin, Germany Country：Germany
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擬似基質を用いる基質特異性変換
荘司長三
第12回バイオ関連化学シンポジウム
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Event date： 2018.9
Language：Japanese Presentation type：Oral presentation (general)
Venue：大阪 Country：Japan
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偽物の基質による酵素の誤作動を利用する物質変換 Invited
荘司長三
新化学技術推進協会（JACI）主催講演会
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Event date： 2018.8
Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京 Country：Japan
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Heme Acquisition Protein HasA with Synthetic Metal Complexes as an Artificial Prosthetic Group
O.Shoji
The 68th Conference of Japan Society of Coordination Chemistry
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Event date： 2018.7
Language：English Presentation type：Oral presentation (general)
Country：Japan
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Heme Acquisition Protein HasA with Metal-Phthalocyanine and 5,15-DiphenylporphyrinDerivatives as an Artificial Prosthetic Group International conference
O.Shoji
Tenth International Conference on Porphyrins and Phthalocyanines (ICPP-10)
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Event date： 2018.7
Language：English Presentation type：Oral presentation (general)
Venue：Munich, Germany Country：Germany
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生体触媒の基質誤認識を利用する高難度水酸化反応 Invited
荘司長三
東京大学大学院薬学系研究科天然物化学教室セミナー
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Event date： 2018.5
Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京 Country：Japan
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Assisted by Decoy Molecules Invited International conference
O. Shoji
3rd Japan - UK Joint Symposium on Coordination Chemistry
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Event date： 2018.4 - 2018.5
Language：English Presentation type：Oral presentation (invited, special)
Venue：St Andrews, UK. Country：United Kingdom
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Hydroxylation of gaseous alkanes and benzene catalyzed by cytochrome P450BM3 using decoy molecules as a substrate analogue International conference
O. Shoji, Y. Watanabe
255thACS National Meeting & Exposition
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Event date： 2018.3
Language：English Presentation type：Oral presentation (general)
Venue：New Orleans, USA Country：United States
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疑似基質による酸化酵素の誤作動誘起と高難度水酸化反応
荘司長三、小野田浩宜、元川竜平、中川洋、渡辺芳人
第7回名古屋大学シンクロトロン光研究センターシンポジウム
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Event date： 2018.1
Language：Japanese Presentation type：Oral presentation (general)
Venue：名古屋 Country：Japan
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疑似基質による酸化酵素の高活性化と不活性アルカン類の水酸化
荘司長三、有安真也、鈴木和人、中村大、唐澤昌之、愛場雄一、渡辺芳人
第50回酸化反応討論会
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Event date： 2017.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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疑似基質による酵素活性化とメタン水酸化
荘司 長三
50周年記念プレシンポジウム～CREST・さきがけ「革新的触媒」メタン資源利用に向けて～
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Event date： 2017.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Hydroxylation of Nonnative Substrate Catalyzed by Cytochrome P450BM3 using Decoy Molecules
O. Shoji
11th Japan-China Joint Symposium on Metal Cluster Compounds
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Event date： 2017.10
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Nonnative Substrate Hydroxylation Catalyzed by Cytochrome P450BM3 without any Mutagenesis
O. Shoji
The 2nd Japan-US Bilateral Meeting on Coordination Chemistry
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Event date： 2017.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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疑似基質による生体触媒の誤作動誘起と高難度酸化反応
荘司 長三
第57回オーロラセミナー
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Event date： 2017.7
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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ヘム獲得蛋白質と合成金属錯体の複合体による緑膿菌の増殖抑制
荘司 長三
第27回金属の関与する生体関連反応シンポジウム（SRM2017）
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Event date： 2017.6
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Gaseous alkane and Benzene Hydroxylation Catalyzed by Cytochrome P450BM3 with the assistance of Decoy Molecules International conference
O. Shoji
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Event date： 2017.6
Language：English Presentation type：Oral presentation (invited, special)
Country：Viet Nam
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フッ素含有疑似基質による酸化酵素の誤作動誘起と高難度酸化反応
荘司 長三
第１４回フッ素相模セミナー
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Event date： 2017.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Development of Biocatalysts for Extremely Difficult Oxidation Reactions
O. Shoji
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Event date： 2017.5
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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生体触媒の誤作動を利用するガス状アルカンの触媒的変換反応
荘司 長三
日本化学会 第97春季年会 (2017)
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Event date： 2017.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkane Hydroxylation Catalyzed by Cytochrome P450BM3 Assisted by Next Generation Decoy Molecules International conference
O. Shoji
SABIC-2017
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Event date： 2017.1
Language：English Presentation type：Oral presentation (keynote)
Country：India
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酸化酵素の誤作動を利用するバイオ触媒系の創成
荘司 長三
ＪＸエネルギー株式会社講演会
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Event date： 2016.12
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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酵素の誤作動を誘起する偽の基質と高難度酸化反応
荘司 長三
第８回 岩澤コンファレンス「サステイナブル社会のための最先端触媒化学・表面科学」
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Event date： 2016.12
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Growth Inhibition of Pseudomonas Aeruginosa by Hasa with Synthetic Metal Complexes and A Novel Elimination System of Bacteria by Photo-Irradiation International conference
O. Shoji, C. Shirataki, Y. Shisaka, H. Uehara, Y. Iwai, A. Nakashima, M. Terada, S. Ozaki, H. Sugimoto, Y. Shiro, Y. Watanabe
AsBIC8
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Event date： 2016.12
Language：English Presentation type：Oral presentation (invited, special)
Country：New Zealand
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フッ素置換疑似基質による生体触媒の反応制御
荘司 長三
フルオラス科学研究会第９回シンポジウム
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Event date： 2016.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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酵素の誤作動を利用する高難度物質変換
荘司 長三
東京理科大学講演会
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Event date： 2016.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Non-native Substrate Hydroxylation catalyzed by Cytochrome P450s Utilizing False Recognition of Target Substrates
O. Shoji
Japan-Korea-Taiwan Bioinorganic Chemistry Symposium
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Event date： 2016.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Construction of Biocatalysts Based on Substrate Misrecognition of Enzymes
O. Shoji
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Event date： 2016.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Hydroxylation of Non-Native Substrates by Tricking the Substrate Recognition of Cytochrome P450s International conference
O. Shoji
Japan-Australia Joint Symposium on Coordination Chemistry (JAJSCC2016)
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Event date： 2016.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkane Hydroxylation by Cytochrome P450s Assisted by Decoy Molecules International conference
O. Shoji
SeleCa Workshop on Artificial Metalloenzymes
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Event date： 2016.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Germany
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Gaseous alkane hydroxylation by tricking the substrate recognition of cytochrome P450s International conference
O. Shoji
FOR 1405 Symposium with external guests at the RWTH Aachen University
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Event date： 2016.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Germany
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疑似基質による生体触媒の誤作動と高難度酸化反応
荘司 長三、叢 志奇、柳澤颯太、杉本 宏、城 宜嗣、渡辺 芳人
第26回バイオ・高分子シンポジウム
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Event date： 2016.7
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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疑似基質による生体触媒の反応制御
荘司長三
第１回産総研中国センター酵素研究セミナー
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Event date： 2016.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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疑似基質による反応空間制御とガス状アルカンの水酸化反応
荘司長三
第16回日本蛋白質科学会年会
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Event date： 2016.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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外部添加因子による生体触媒の反応空間制御
荘司長三
分子研研究会「金属錯体の非対称配位圏設計と異方集積化が拓く新物質創成科学」
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Event date： 2016.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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生体触媒の基質誤認識を利用する不活性炭化水素へ酸素原子挿入反応触媒系の開発
荘司長三
新学術領域研究「精密制御反応場」第1回公開シンポジウム
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Event date： 2016.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Activation of cytochrome P450BM3 by decoy molecules for gaseous alkane hydroxylation International conference
O. Shoji, Y. Watanabe
Pacifichem 2015
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Event date： 2015.12
Language：English Presentation type：Oral presentation (invited, special)
Country：United States
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次世代疑似基質によるシトクロムP450BM3の活性化とガス状アルカンの水酸化
荘司長三、叢 志奇、杉本 宏、城 宜嗣、渡辺芳人
第48回酸化反応討論会
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Event date： 2015.10
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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野生型シトクロムP450BM3によるガス状アルカンの水酸化反応を可能とする次世代疑似基質
荘司長三、叢 志奇、笠井千枝、杉本 宏、城 宜嗣、渡辺芳人
第9回バイオ関連化学シンポジウム
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Event date： 2015.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Hydroxylation of Gaseous Alkanes Catalyzed By Cytochrome P450BM3 Triggered By Decoy Molecules International conference
O. Shoji, Y. Watanabe
BIOTRANS2015
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Event date： 2015.7
Language：English Presentation type：Poster presentation
Country：Austria
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Growth inhibition of Pseudomonas aeruginosa by HasA with metal-phthalocyanine and a novel elimination system of bacteria by photo-irradiation International conference
O. Shoji, C. Shirataki, Y. Iwai, A. Nakashima, M. Terada, S. Ozaki, H. Sugimoto, Y. Shiro, Y. Watanabe
ICBIC17
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Event date： 2015.7
Language：English Presentation type：Oral presentation (invited, special)
Country：China
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Non-native substrate hydroxylation catalyzed by cytochrome P450BM3 triggered by decoy molecules International conference
O. Shoji, Z. Cong, H. Sugimoto, Y. Shiro, Y. Watanabe
"Metals in Biology" in Wako
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Event date： 2015.6
Language：English Presentation type：Poster presentation
Country：Japan
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Hydroxylation of non-native substrates catalyzed by wild-type P450s assisted by decoy molecules International conference
O. Shoji
19th International Conference on Cytochrome P450
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Event date： 2015.6
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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緑膿菌の鉄獲得機構を逆手に取った新規殺菌法の開発
荘司長三
第63回日本化学療法学会総会
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Event date： 2015.6
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Use of Decoy Molecules as a Reaction Accelerator for the Hydroxylation of Gaseous Alkanes Catalyzed by Cytochrome P450s
O. Shoji
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Event date： 2015.3
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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偽のヘム鉄獲得蛋白質を利用する緑膿菌の増殖阻害
荘司長三
第49回緑膿菌感染症研究会
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Event date： 2015.2
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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酸化酵素の誤作動を誘起する次世代疑似基質の開発とガス状アルカンの水酸化
荘司長三
分子研研究会「生物無機化学の最先端と今後の展望：金属と生体分子の作用機序解明とモデル化および応用への展開」
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Event date： 2015.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Hydroxylation of non-native substrates by wild-type cytochrome P450s assisted by decoy molecules International conference
O. Shoji, Y. Watanabe
the Active Enzyme Molecule 2014
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Event date： 2014.12
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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疑似基質による野生型シトクロムP450の誤作動誘起と不活性炭化水素の水酸化反応
荘司長三、渡辺芳人
第44回石油・石油化学討論会
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Event date： 2014.10
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Monooxygenation of Nonnative Substrates Catalyzed by Wild-type Cytochrome P450s International conference
O. Shoji, Y. Watanabe
The 12th International Symposium on Cytochrome P450 Biodiversity and Biotechnology
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Event date： 2014.9
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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改変鉄獲得タンパク質による緑膿菌の増殖阻害
荘司長三、白瀧千夏子、岩井佑介、中島彩夏、寺田光良、小崎紳一、杉本 宏、城 宜嗣、渡辺芳人
錯体化学会第64回討論会
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Event date： 2014.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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疑似基質による野生型酵素の誤作動誘起と不活性炭化水素の水酸化反応
荘司長三、渡辺芳人
第１０回触媒化学融合研究センター講演会
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Event date： 2014.7
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkane Hydroxylation by Wild-Type Cytochrome P450BM3 bearing Decoy Molecules International conference
O. Shoji, J. Yokobori, T. Kunimatsu, N. Kawakami, Zhiqi Cong, Y. Watanabe
ICPP-8
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Event date： 2014.6
Language：English Presentation type：Oral presentation (invited, special)
Country：Turkey
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フッ素置換基質による生体触媒の誤作動誘起と物質変換への利用
荘司長三、渡辺芳人
2014年研究会「金属新機能場の開発を目指して」
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Event date： 2014.2
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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生体触媒の誤作動状態を逆手に取る物質変換
荘司長三、渡辺芳人
新学術領域研究「分子活性化」第６回公開シンポジウムプログラム
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Event date： 2014.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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生体触媒の誤作動状態を利用する物質変換
荘司長三、渡辺芳人
蛋白研セミナー：蛋白質の機能デザインに向けた実験と理論のインタープレー
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Event date： 2014.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkanes and Benzene Hydroxylation by Wild-type Cytochrome P450BM3 Induced by Perfluorinated Carboxylic Acids
The 3rd International Conference on the MEXT Project of Integrated Research on Chemical Synthesis
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Event date： 2014.1
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkane Hydroxylation Catalyzed by Cytochrome P450BM3 by Tricking Its Substrate Recognition Using Decoy Molecules
6th Japan-Korea Seminars on Biomolecular Science : Experiments and Simulation
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Event date： 2013.11
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Hydroxylation of Inert Organic Molecules by Cytochrome P450s Assisted by Decoy Molecules
The 2nd Japan-France Coordination Chemistry Symposium
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Event date： 2013.11
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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Hydroxylation of Non-native Substrates by Wild-type Cytochrome P450BM3 assisted by Decoy Molecules
More details
Event date： 2013.11
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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疑似基質により誘起される生体触媒の誤作動状態を利用するバイオ触媒反応
荘司長三、渡辺芳人
第６回 ChemBioハイブリッドレクチャー
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Event date： 2013.11
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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フッ素置換基質を疑似基質として利用する長鎖脂肪酸水酸化酵素よるガス状アルカンの水酸化反応
荘司長三、川上了史、渡辺芳人
錯体化学会第63回討論会
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Event date： 2013.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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野生型シトクロムP450BM3によるベンゼン及び一置換ベンゼンの水酸化
荘司長三、國松辰弥、川上了史、渡辺芳人
第6回バイオ関連化学シンポジウム
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Event date： 2013.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Ethane and Benzene Hydroxylation by Wild-type Cytochrome P450BM3 Assisted by Decoy Molecules International conference
O. Shoji, T. Kunimatsu, N. Kawakami, Y. Watanabe
, 16th International Conference on Biological Inorganic Chemistry (ICBIC16)
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Event date： 2013.7
Language：English Presentation type：Oral presentation (invited, special)
Country：France
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Gaseous Alkanes and Benzene Hydroxylation by Wild-Type Cytochrome P450BM3 Assisted by Decoy Modules International conference
O. Shoji, N. Kawakami, T. Kunimatsu, Y. Watanabe
The 18th International Conference on Cytochrome P450
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Event date： 2013.6
Language：English Presentation type：Poster presentation
Country：United States
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シトクロムP450BM3の誤作動を逆手に取るアルカン類の水酸化反応
荘司長三、川上了史、國松辰弥、渡辺芳人
平成25年度 P450とUGT/SULT 研究会
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Event date： 2013.6
Language：Japanese Presentation type：Poster presentation
Country：Japan
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Use of Enzyme Malfunction for Small Alkane Hydroxylation International conference
O. Shoji, Y. Watanabe
The 15th joint IRTG SYMPOSIUM between University of Münster - Nagoya University
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Event date： 2013.5
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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酵素の誤認識を利用するバイオ触媒の開発
荘司長三
若い世代の特別講演会 日本化学会第93春季年会（2013）
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Event date： 2013.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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有機化学利用をめざした生体触媒の反応制御
荘司長三
特別企画講演 日本化学会第93春季年会（2013）
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Event date： 2013.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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蛋白質の誤作動を利用する触媒システム開発と新規機能への展開
荘司長三
分子研研究会「生体配位化学の最前線と展望」
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Event date： 2013.2
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Development of Biocatalysts based on Substrate Misrecognition of Cytochrome P450s International conference
O. Shoji, Y. Watanabe
50th Anniversary Symposium on Cytochrome P450 in Fukuoka
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Event date： 2012.12
Language：English Presentation type：Oral presentation (invited, special)
Country：Japan
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不斉炭素を持つ基質類似分子による酸化酵素のエナンチオ選択性制御
荘司長三
第45回 酸化反応討論会
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Event date： 2012.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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酸化酵素の誤作動を逆手に取ったバイオ触媒系の開発
荘司長三
第25回 生物無機化学夏季セミナー
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Event date： 2012.8
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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Gaseous Alkane Hydroxylation Catalyzed by Cytochrome P450BM3 by Tricking its Substrate Recognition Using Decoy Molecules International conference
O. Shoji, Y. Watanabe
Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
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Event date： 2012.7
Language：English Presentation type：Oral presentation (invited, special)
Country：Korea, Republic of
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長鎖脂肪酸水酸化酵素の基質誤認識誘導によるガス状アルカンの水酸化反応
荘司長三
日本化学会第92春季年会（2012）
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Event date： 2012.3
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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疑似基質による酸化酵素の誤作動とガス状アルカンの水酸化反応
荘司長三
平成23年度 高難度選択酸化反応研究会シンポジウム
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Event date： 2012.1
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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水分子の排除をトリガーとするシトクロムP450の水酸化反応と疑似基質による基質多様性付加
荘司長三
中性子産業利用促進協議会 生体構造研究会
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Event date： 2011.12
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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自己完結型過酸化水素駆動シトクロムP450による一酸素原子添加反応
荘司長三、藤城貴史、木本 洋、田中 翔太、堀 あゆ美、西尾 洸祐、杉本 洋、城 宜嗣、渡辺芳人
第44回酸化反応討論会
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Event date： 2011.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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自己完結型過酸化水素駆動シトクロムP450の構築
荘司 長三、藤城 貴史、木本 洋、杉本 宏、城 宜嗣、渡辺 芳人
錯体化学会 第61回討論会
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Event date： 2011.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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細菌由来シトクロムP450 の基質誤認識を利用するバイオ触媒系の開発
荘司 長三、川上了史、藤城 貴史、杉本 宏、永野 真吾、城 宜嗣、渡辺 芳人
第5回バイオ関連化学シンポジウム
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Event date： 2011.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Hydroxylation of Gaseous Alkanes by Cytochrome P450 using Substrate Recognition Tricks International conference
O. Shoji, T. Kunimatsu, N. Kawakami, Y. Watanabe
ICBIC15
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Event date： 2011.8
Language：English Presentation type：Oral presentation (general)
Country：Canada
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Crystal Structures of Hydrogen Peroxide-Dependent Cytochrome P450s Including Decoy Molecules and Oxidation Reaction of Non-natural Substrates International conference
O. Shoji
17th International Conference on Cytochrome P450
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Event date： 2011.6
Language：English Presentation type：Oral presentation (general)
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基質認識トリックを利用する新規バイオ触媒系の開発
荘司 長三
統合物質創製化学推進事業 第2 回若手研究会
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Event date： 2011.5
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Construction of Biocatalysts using a Decoy Molecule of P450s
Seminar at RWTH Aachen - Biotechnologie
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Event date： 2010.12
Language：English Presentation type：Oral presentation (invited, special)
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Gaseous Alkane Hydroxylation Catalyzed by Cytochrome P450 with Substrate Recognition Tricks International conference
Seminar at Universitt Dortmund
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Event date： 2010.12
Language：English Presentation type：Oral presentation (invited, special)
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A novel approach to utilize cytochrome P450s as a biocatalyst International conference
IRTG seminar
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Event date： 2010.12
Language：English Presentation type：Oral presentation (invited, special)
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シトクロムP450の基質認識トリックを利用するガス状アルカンの水酸化反応
第１回統合物質シンポジウム
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Event date： 2010.12
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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細菌由来シトクロムP450による飽和炭化水素の水酸化反応
荘司 長三、川上 了史、藤城 貴史、杉本 宏、永野 真吾、城 宜嗣、渡辺 芳人
第60回錯体化学討論会
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Event date： 2010.9
Language：Japanese Presentation type：Poster presentation
Country：Japan
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シトクロムP450のデコイ基質を利用する基質特異性変換
荘司 長三、藤城 貴史、田中 翔太、川上 了史、杉本 宏、永野 真吾、城 宜嗣、渡辺 芳人
第4回バイオ関連化学シンポジウム
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Event date： 2010.9
Language：Japanese Presentation type：Poster presentation
Country：Japan
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シトクロムP450の基質特異性変換と反応制御
荘司 長三、藤城 貴史、田中 翔太、杉本 宏、永野 真吾、城 宜嗣、渡辺 芳人
第37回 生体分子科学討論会
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Event date： 2010.6
Language：Japanese Presentation type：Poster presentation
Country：Japan
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第４２回 酸化反応討論会
荘司長三、藤城貴史、田中翔太、永野真吾、城宜嗣、渡辺芳人
シトクロムP450の基質特異性を変換する新規手法の開発
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Event date： 2009.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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Monooxidations of Non-natural Substrates by Hydrogen Peroxide-Dependent Cytochrome P450: Tricking the Substrate Recognition of Cytochrome P450BSβ by Decoy Molecules International conference
16 th International Conference on Cytochrome P450 (ICC2009)
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Event date： 2009.7
Language：English Presentation type：Poster presentation
Country：Japan
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Crystal Structures of the Substrate-Free and the Decoy Molecule-bound Forms of Cytochrome P450BSβ International conference
14th International Conference on Biological Inorganic Chemistry (ICBIC14)
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Event date： 2009.6
Language：English
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Creating Semi-Artificial Enzymes by Tricking the Substrate Recognition of Cytochrome P450BSβ International conference
7th joint IRTG Symposium University of Münster and Nagoya University
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Event date： 2009.5
Language：English Presentation type：Oral presentation (invited, special)
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過酸化水素駆動型シトクロムP450BSによる芳香環水酸化反応
荘司長三、WIESE, Christian、藤城貴史・WÜNSCH, Bernhard、永野真吾、城宜嗣、渡辺芳人
日本化学会第89春季年会
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Event date： 2009.3
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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酵素の基質誤認識を利用する過酸化水素駆動型バイオ触媒の開発
荘司長三
大学間連携事業第3回若手フォーラム
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Event date： 2008.11
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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ヘム酵素反応空間の外部添加因子による修飾と反応制御
荘司長三
第39回中部化学関係学協会支部連合協議会秋季大会
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Event date： 2008.11
Language：Japanese Presentation type：Oral presentation (invited, special)
Country：Japan
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枯草菌由来の過酸化水素駆動型シトクロムP450による非天然基
荘司長三、藤城貴史、中島洋、松永勇、永野真吾、城宜嗣、渡辺芳人
第102回触媒討論会
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Event date： 2008.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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デコイ分子により誘起されるシトクロムP450BSbの基質誤認識を利用する非天然基質の酸化反応
荘司長三、藤城貴史、永野真吾、城宜嗣、渡辺芳人
第3回バイオ関連化学合同シンポジウム2008
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Event date： 2008.9
Language：Japanese Presentation type：Oral presentation (general)
Country：Japan
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"Hydroxylation of Nonnative Substrates by Cytochrome P450BM3 Exploiting Decoy Molecules International conference
O.Shoji
2019.9.26
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Language：English Presentation type：Symposium, workshop panel (nominated)
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金属酵素の誤作動を利用する物質変換 Invited International conference
荘司長三
新学術「生合成リデザイン」第５回公開シンポジウム 2018.12.15
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Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：千葉
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金属蛋白質の対象誤認識を利用する機能改変 Invited International conference
荘司長三
新学術領域研究「高難度物質変換反応の開発を指向した精密制御反応場の創出」第６回公開シンポジウム 2019.1.21
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Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：京都
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酸化酵素の誤作動を誘起する擬似基質を用いる物質変換 Invited International conference
荘司長三
分子研研究会「錯体化学を基盤とした階層構造制御と機能発現」 2019.3.3
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Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：愛知
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酸化酵素の誤作動を誘起する低分子化合物による基質特異性変換 Invited International conference
荘司長三
日本におけるケミカルバイオロジーの新展開第189委員会 平成30年度 第4回定例会 2019.3.6
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Language：Japanese Presentation type：Symposium, workshop panel (nominated)
Venue：大阪市
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酸化酵素の誤作動を利用する物質変換 Invited International conference
荘司長三
酵素工学研究会第80回講演会 2018.11.16
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Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京
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酵素の誤作動を誘起する分子の開発と物質変換 Invited International conference
荘司長三
日本化学会東北支部山形地区講演会—生体外で活躍するタンパク質— 2019.7.12
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Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：山形市
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疑似基質による酸化酵素の高活性化と不活性アルカン類の水酸化 International conference
荘司長三, 有安真也, 鈴木和人, 中村大, 唐澤昌之, 愛場雄一, 渡辺芳人
第50回酸化反応討論会 2017.11.11
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Language：Japanese Presentation type：Oral presentation (general)
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疑似基質による酸化酵素の誤作動誘起と高難度水酸化反応 International conference
荘司長三, 小野田浩宜, 元川竜平, 中川洋, 渡辺芳人
第7回名古屋大学シンクロトロン光研究センターシンポジウム 2018.1.19
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Language：Japanese Presentation type：Oral presentation (general)
Venue：名古屋
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疑似基質による酵素活性化とメタン水酸化 International conference
荘司 長三
50周年記念プレシンポジウム～CREST・さきがけ「革新的触媒」メタン資源利用に向けて～ 2017.11.10
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Language：Japanese Presentation type：Oral presentation (general)
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疑似基質による生体触媒の誤作動誘起と高難度酸化反応 International conference
荘司 長三
第57回オーロラセミナー 2017.7.23
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Language：Japanese Presentation type：Oral presentation (invited, special)
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生体触媒の誤作動を利用するガス状アルカンの触媒的変換反応 International conference
荘司 長三
日本化学会 第97春季年会 (2017) 2017.3.16
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Language：Japanese Presentation type：Oral presentation (invited, special)
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生体触媒の基質誤認識を利用する高難度水酸化反応 Invited International conference
荘司長三
東京大学大学院薬学系研究科天然物化学教室セミナー 2018.5.18
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Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京
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擬似基質を用いる基質特異性変換 International conference
荘司長三
第12回バイオ関連化学シンポジウム 2018.9.9
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Language：Japanese Presentation type：Oral presentation (general)
Venue：大阪
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偽物の基質による酵素の誤作動を利用する物質変換 Invited International conference
荘司長三
新化学技術推進協会（JACI）主催講演会 2018.8.23
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Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：東京
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ベンゼンをフェノールに変換するバイオ触媒系の開発 International conference
荘司長三
第49回中部化学関係学協会支部連合秋季大会 2018.11.3
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Language：Japanese Presentation type：Public lecture, seminar, tutorial, course, or other speech
Venue：名古屋
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ヘム獲得蛋白質と合成金属錯体の複合体による緑膿菌の増殖抑制 International conference
荘司 長三
第27回金属の関与する生体関連反応シンポジウム（SRM2017） 2017.6.16
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Language：Japanese Presentation type：Oral presentation (general)
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フッ素含有疑似基質による酸化酵素の誤作動誘起と高難度酸化反応 International conference
荘司 長三
第１４回フッ素相模セミナー 2017.6.1
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Language：Japanese Presentation type：Oral presentation (invited, special)
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シトクロムP450の基質誤認識を利用する菌体内物質変換 Invited International conference
荘司長三
第19回日本蛋白質科学会年会第71回日本細胞生物学会大会合同年次大会 2019.6.24
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Language：Japanese Presentation type：Oral presentation (invited, special)
Venue：兵庫
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Whole-Cell Biotransformation Catalysed by Intracellular Cytochrome P450BM3 Activated by Decoy Molecules Invited
Osami Shoji
ArtZymes 2.0 2019.8.9
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Language：English Presentation type：Oral presentation (invited, special)
Venue：Basel
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Use of Decoy Molecules to Trick Cytochrome P450s International conference
O.Shoji
2019.9.7
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Language：English Presentation type：Symposium, workshop panel (nominated)
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Use of Decoy Molecules to Trick Cytochrome P450BM3 into Hydroxylating Nonnative Substrates
Osami Shoji
the 21st International Conference on Cytochrome P450 2019.6.23
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Language：English Presentation type：Oral presentation (general)
Venue：Brisbane
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Nonnative Substrate Hydroxylation Catalyzed by Cytochrome P450BM3 without any Mutagenesis International conference
O. Shoji
The 2nd Japan-US Bilateral Meeting on Coordination Chemistry 2017.9.15
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Language：English Presentation type：Oral presentation (invited, special)
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Hydroxylation of Nonnative Substrates Catalyzed by Wild-type Cytochrome P450BM3 with Decoy Molecules Invited
O.Shoji
The 13th International Symposium on Organic Reactions 2018.11.21
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Language：English Presentation type：Oral presentation (invited, special)
Venue：Hsinchu, Taiwan
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Facilitated by Decoy Molecules Invited International conference
Osami Shoji
New Frontier in Protein Design & Engineering 2019.3.15
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Language：English Presentation type：Symposium, workshop panel (nominated)
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Exploiting Decoy Molecules
Osami Shoji
2019 Korea-Taiwan-Japan Bioinorganic Chemistry Symposium 2019.11.12
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Language：English Presentation type：Oral presentation (general)
Venue：Taichung City, Taiwan
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Assisted by Decoy Molecules Invited
Osami Shoji
15th International Symposium on Applied Bioinorganic Chemistry (ISABC15) 2019.6.23
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Language：English Presentation type：Oral presentation (keynote)
Venue：Nara
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Hydroxylation of Nonnative Substrates Catalyzed by Cytochrome P450BM3 Assisted by Decoy Molecules Invited
O. Shoji
3rd Japan - UK Joint Symposium on Coordination Chemistry 2018.4.30
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Language：English Presentation type：Oral presentation (invited, special)
Venue：St Andrews, UK.
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Hydroxylation of Nonnative Substrates by Cytochrome P450BM3 Exploiting Decoy Molecules
Osami Shoji
19th International Conference on Biological Inorganic Chemistry (ICBIC-19) 2019.8.11
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Language：English Presentation type：Oral presentation (general)
Venue：Interlaken
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HYDROXYLATION OF NONNATIVE SUBSTRATES BY CYTOCHROME P450BM3 EXPLOITING DECOY MOLECULES Invited
Osami Shoji
12th China Japan Joint Symposium on Metal Cluster Compounds (CJJSMCC2019) 2019.10.25
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Language：English Presentation type：Symposium, workshop panel (nominated)
Venue：Taichung City, Taiwan
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Hydroxylation of Nonnative Substrate Catalyzed by Cytochrome P450BM3 using Decoy Molecules International conference
O. Shoji
11th Japan-China Joint Symposium on Metal Cluster Compounds 2017.10.7
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Language：English Presentation type：Oral presentation (invited, special)
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 with Decoy Moleculues Invited
O.Shoji
2nd China-Japan Joint Symposium on the Biosynthesis of Natural Products 2019.1.14
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Language：English Presentation type：Oral presentation (invited, special)
Venue：Guangzhou, China
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 Facilitated by Decoy Moleculues
O.Shoji
FHI-JST Joint Symposium,Current Topics and Challenges for Innovative Catalysts 2018.10.31
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Language：English Presentation type：Oral presentation (general)
Venue：Berlin, Germany
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Hydroxylation of Non-native Substrates Catalyzed by Cytochrome P450BM3 Activated by External Additives Invited International conference
Osami Shoji
Core-to-Core Symposium Elements Function for Transformative Catalysis and Materials 2019.2.7
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Language：English Presentation type：Symposium, workshop panel (nominated)
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Hydroxylation of gaseous alkanes and benzene catalyzed by cytochrome P450BM3 using decoy molecules as a substrate analogue
O. Shoji, Y. Watanabe
255thACS National Meeting & Exposition 2018.3.18
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Language：English Presentation type：Oral presentation (general)
Venue：New Orleans, USA
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Heme Acquisition Protein HasA with Synthetic Metal Complexes as an Artificial Prosthetic Group International conference
O.Shoji
The 68th Conference of Japan Society of Coordination Chemistry 2018.7.28
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Language：English Presentation type：Oral presentation (general)
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Heme Acquisition Protein HasA with Metal-Phthalocyanine and 5,15-DiphenylporphyrinDerivatives as an Artificial Prosthetic Group
O.Shoji
Tenth International Conference on Porphyrins and Phthalocyanines (ICPP-10) 2018.7.1
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Language：English Presentation type：Oral presentation (general)
Venue：Munich, Germany
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Gaseous Alkane Hydroxylation Catalyzed by Cytochrome P450BM3 Assisted by Next Generation Decoy Molecules
O. Shoji
SABIC-2017 2017.1.7
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Language：English Presentation type：Oral presentation (keynote)
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Gaseous alkane and Benzene Hydroxylation Catalyzed by Cytochrome P450BM3 with the assistance of Decoy Molecules
O. Shoji
2017.6.8
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Language：English Presentation type：Oral presentation (invited, special)
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Development of Biocatalysts for Extremely Difficult Oxidation Reactions International conference
O. Shoji
2017.5.12
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Language：English Presentation type：Oral presentation (invited, special)
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Cheating Cytochrome P450BM3 into Hydroxylating Non-Native Substrates by Exploiting its Substrate Misrecognition Invited International conference
O. Shoji
Let's leap! Challenges in Organic Chemistry 2019.4.20
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Language：English Presentation type：Public lecture, seminar, tutorial, course, or other speech
Research Project for Joint Research, Competitive Funding, etc.
Research Project for Joint Research, Competitive Funding, etc. 2
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石油系原料からの高付加価値品製造に関する研究
2016.6 - 2017.3
企業からの受託研究
瀬川敦司、牧田智裕
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シトクロムP450による光駆動型酸化反応を可能にする金属錯体連結疑似基質の開発
2015.4 - 2016.3
企業からの受託研究
KAKENHI (Grants-in-Aid for Scientific Research)
KAKENHI (Grants-in-Aid for Scientific Research) 18
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Grant number：24K22051 2024.6 - 2026.3
Grants-in-Aid for Scientific Research Grant-in-Aid for Challenging Research (Exploratory)
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Authorship：Principal investigator
Grant amount：\6370000 （ Direct Cost: \4900000 、 Indirect Cost：\1470000 ）
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Grant number：21H04704 2021.4 - 2024.3
Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (A)
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Authorship：Principal investigator
Grant amount：\42900000 （ Direct Cost: \33000000 、 Indirect Cost：\9900000 ）
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Material Transformation Using Biocatalysts Assisted by External Additives
Grant number：15H05806 2015.6 - 2020.3
Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
Shoji Osami
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Authorship：Principal investigator
Grant amount：\35880000 （ Direct Cost: \27600000 、 Indirect Cost：\8280000 ）
We found that cytochrome P450BM3 starts to catalyze hydroxylation of nonnative substrates in the presence of inert dummy substrates (decoy molecules). Recently, we have demonstrated that various carboxylic acids modified with amino acids (N-acyl amino acids) having a completely different structure from fatty acids can serve as decoy molecules. Benzene was more efficiently hydroxylated in the presence of these decoy molecules. We also have demonstrated that the heme acquisition protein HasA secreted by Pseudomonas aeruginosa can accommodate Iron(III)-5,15-diphenylporphyrin and its derivatives including Fe-diaza-DPP without any structural perturbation. Crystal structure analysis revealed that phenyl groups at the meso-position of the porphyrins extend outside of HasA to avoid steric crowding and are exposed to the solvent. Iron(III)- and cobalt(III)-tetraphenylporphycenes, which possess bulky phenyl groups, also can be incorporated into HasA.
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Grant number：26708018 2014.4 - 2018.3
Grants-in-Aid for Scientific Research Grant-in-Aid for Young Scientists (A)
Shoji Osami
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Authorship：Principal investigator
Grant amount：\24830000 （ Direct Cost: \19100000 、 Indirect Cost：\5730000 ）
HasA (Heme acquisition system A) is a hemophore secreted by some pathogenic bacteria having a heme acquisition system (Has system) such as Pseudomonas aeruginosa. We have found that HasA can capture several synthetic metal complexes other than heme such as iron-salophen and iron-phthalocyanine. The crystal structures of HasA harboring iron-salophen and iron-phthalocyanine showed only small structural perturbations compared with that of HasA with heme. We also found that HasA bound to iron-phthalocyanine strongly inhibited HasA-mediated heme acquisition. Furthermore, we have demonstrated that Pseudomonas aeruginosa can be eliminated by photo-irradiation at 680 nm in the presence of HasA bound to gallium-phthalocyanine due to generation of singlet oxygen.
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Dynamic Element-Effect Design for Unconventional Molecular Functions
Grant number：22K21346 2022.12 - 2029.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Fund for the Promotion of Joint International Research (International Leading Research )
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Authorship：Coinvestigator(s)
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Grant number：22H05119 2022.6 - 2027.3
日本学術振興会 科学研究費助成事業 学術変革領域研究(A)
葛山 智久, 内山 真伸, 丸山 千登勢, 寺田 透, 渡辺 賢二, 勝山 陽平, 山崎 真巳, 脇本 敏幸, 大栗 博毅, 淡川 孝義, 荘司 長三
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Authorship：Coinvestigator(s)
天然化合物は「探す」ものという天然物化学分野で半世紀以上続いてきた既成概念から脱却し、天然化合物の設計図である生合成遺伝子の機能を予知し再構成して天然化合物を人工的に「創り出す」ものとする根本的な変革を先導する。そのため、既存の方法では解析が追いつかず、解析されぬまま爆発的に蓄積し続ける未利用資源とも言うべきゲノム情報から未知の有益な配列情報を情報科学的アプローチで効率的に抽出し、さらに生物合成と化学合成の手法で未踏の天然化合物の生産を可能にすることを目指す。
計画班メンバーによるキックオフミーティングを、2022年7月2日に、東京大学大学院農学生命科学研究科で行い、今後の研究方針について意見交換を行った。
本領域の共催企画として2022年8月16日に札幌生合成国際シンポジウムを北海道大学薬学部臨床薬学講義室で開催した。 スイスETHのJorn Piel教授に加え、ボン大学のJeroen Dickschat 教授や、本領域の計画班メンバーらが講演を行った。ハイブリッド形式で実施し、アメリカやシンガポールからの参加者を含む80名近い参加者が出席した。
2022年8月26日に、東京大学薬学部総合研究棟2階講堂において第1回若手シンポジウムを開催した。本シンポジウムでは、 第1部で、計画班を中心とした若手研究発表会を非公開で行い、第2部で、公開シンポジウムとして、「予知生合成科学」の研究領域の説明と特別講演を開催した。
2022年度日本放線菌学会大会では、共催シンポジウムとして、Inha Universityの Eung-Soo Kim教授を特別講演の講師としてお招きし、ご講演いただいた。
計画班の分担者である東京大学大学院薬学系研究科助教の牛丸理一郎博士が、2022年10月に生合成研究についての意見交換と講演のためアメリカの10大学を訪問した。本研究領域では、前半の3つの大学での講演と意見交換についてサポートを行った。
2023年1月28日に、東京大学農学部において第1回公開シンポジウムを開催した。計画班研究代表者11名が研究計画と研究成果について発表した。最新の成果や今後の研究の方向性に関する活発な議論が行われた。2023年3月15日に、日本農芸化学会大会で、「生合成研究の変革を目指して ～実験科学と計算科学の融合への挑戦～」というシンポジウムを開催し、本領域の計画班から6名が発表した。
初年度は計画班だけによる研究が予定していたメンバーでスタートした。
速やかに領域のWebページを作成し、領域の研究概要や、各班員の研究内容を公開することができた。このwebページやシンポジウムで、公募班の研究概要を伝えることで、予定していた人数の公募班を立ち上げることができた。国際シンポジウムと学会に海外研究者を招聘し、最先端研究を紹介してもらえたことで、本領域の活性化につながっている。若手研究者を海外に派遣し、本領域における最先端研究を学んだり意見交換したことも、本領域の活性化につながっている。Slackやメールを利用した情報交換は、共同研究を進めるのに大きく貢献している。
各計画班や公募班が、研究計画に従って研究を推進するよう、メールや公開シンポジウムでの班会議などで周知していく。そのため、まずは、公募班の研究内容を明確にするため、図とその説明を作成してもらい、領域のホームページで公開する。これにより、研究領域の意義や研究内容を広く周知し、共同研究の促進を図る。そのため、公募班を加えた、第２回公開シンポジウムを6月10日-11日の日程で、計画班の北海道大学の脇本教授を担当者として開催する。このシンポジウムでは、共同研究の推進を計る目的で、公募班全員の研究内容をショートプレゼンテーションとポスター発表で十分に周知してもらう予定である。また、計画班の若手の分担者には、研究成果と研究計画について発表してもらい、お互いの研究をよく理解し合うことを計画している。
これら若手の啓蒙に加えて、8月には、第２回若手シンポジウムを計画している。ここでは、各班に所属する学生やポスドク、若手研究者に集まってもらい、研究に関するアプリケーションの使い方などの講習会も予定している。また、日中間などの国際間の生合成シンポジウムも積極的に開催する。
2024年2月には、第２回公開シンポジウムを東京大学で開催予定である。ここでは、計画班を中心に最新の研究成果を発表してもらう。
加えて、本研究領域で第一線の成果を挙げている海外の著名な研究者をお呼びして、特別講演を開催し、班員の研究推進のサポートを行う。若手研究者や学生を海外の大学などで行われるサマースクールに通わせたり、海外の著名な研究者の研究室を訪問し、成果発表や討論などを通して、若手の国際交流を図る。研究成果に関しては、本研究領域のホームページで随時公開するとともに、SNSを通じて広く発信する。 -
Grant number：22H05129 2022.6 - 2027.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Transformative Research Areas (A)
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Authorship：Principal investigator
Grant amount：\82030000 （ Direct Cost: \63100000 、 Indirect Cost：\18930000 ）
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Grant number：18H02084 2018.4 - 2021.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
Shoji Osami
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Authorship：Principal investigator
Grant amount：\17420000 （ Direct Cost: \13400000 、 Indirect Cost：\4020000 ）
Pseudomonas aeruginosa, one of the more notorious opportunistic human pathogens, which has been classed with the highest priority level of “critical” by the World Health Organization (WHO). We demonstrated that bacterial heme transport systems can be exploited for the delivery of antimicrobials to the intracellular space of target bacteria with high specificity. We demonstrated that, analogous to heme uptake, HasA can specifically traffic an antimicrobial, gallium phthalocyanine (GaPc), into the intracellular space of Pseudomonas aeruginosa the interaction of HasA with its outer membrane receptor HasR. HasA enables water-insoluble GaPc to be mistakenly acquired by Pseudomonas aeruginosa, permitting its sterilization (>99.99%) by irradiation with near-infrared (NIR) light, irrespective of antibiotic resistance. This specific route of antimicrobial transport enables the efficient sterilization of P. aeruginosa, including its multidrug-resistant strains (MDRP).
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生体触媒の誤作動状態を利用するメタンの直接的メタノール変換
2015.10 - 2021.9
科学技術振興機構(JST) 戦略的創造研究推進事業 多様な天然炭素資源の活用に資する革新的触媒と創出技術
荘司 長三、杉本 宏、久保 稔
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Authorship：Principal investigator
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外部添加因子による生体触媒反応場の制御と高難度物質変換
2015.6 - 2020.3
科学研究費補助金 新学術領域研究(研究領域提案型)
More details
Authorship：Principal investigator
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外部添加因子による生体触媒反応場の制御と高難度物質変換
2015.6 - 2020.3
科学研究費助成事業 新学術領域研究(研究領域提案型)
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Grant type：Competitive
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変性蛋白質の自己集合状態を利用する新規機能性蛋白質の開発
2015.4 - 2016.3
科学研究費補助金
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改変型鉄獲得蛋白質による緑膿菌の鉄獲得阻害と光線力学的反応を併用する殺菌システム
2014.4 - 2018.3
科学研究費補助金 若手研究(A)
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改変型鉄獲得蛋白質による緑膿菌の鉄獲得阻害と光線力学的反応を併用する殺菌システム
2014.4 - 2018.3
日本学術振興会 科学研究費助成事業 若手研究(A)
More details
Grant type：Competitive
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生体触媒の基質誤認識を利用する不活性炭化水素への酸素原子挿入反応触媒系の開発
2013.4 - 2015.3
科学研究費補助金 新学術領域研究(研究領域提案型)
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Authorship：Principal investigator
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Molecular Design of Biocatalysts for Hydroxylation of Small Alkanes
Grant number：24225004 2012.5 - 2017.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (S) Grant-in-Aid for Scientific Research (S)
Watanabe Yoshihito, SHOJI Osami
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Cytochrome P450BM3 (P450BM3) isolated from Bacillus megaterium catalyzes the hydroxylation of long-alkyl-chain fatty acids. We have demonstrated that even wild-type P450BM3 can catalyze the hydroxylation of gaseous alkanes such as ethane and propane as well as benzene by using perfluorinated carboxylic acids (PFCs) as decoy molecules. We also have demonstrated that N-perfluoroacyl amino acids strongly activate wild-type P450BM3 for the hydroxylation of inert alkanes. Furthermore, we showed that substrate-binding-state mimics of hydrogen peroxide-dependent cytochrome P450s prepared by one-point mutagenesis are able to catalyze monooxygenation of non-native substrates. The same mutation was also effective in introducing peroxygenase activity into P450BM3 and P450cam, indicating that a variety of peroxygenases based on P450s can be constructed by one-point mutagenesis.
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酵素の基質誤認識を利用するバイオ触媒の創成
2009.4 - 2012.3
科学研究費補助金 若手研究(A)
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高難度酸化反応を可能とするヘム酵素の創
2006.4 - 2009.3
科学研究費補助金
Industrial property rights
Industrial property rights 8
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高圧化学反応装置
渡辺 芳人、荘司 長三
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Application no：特願2017-195706 Date applied：2017.10
Country of applicant：Domestic
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高圧化学反応装置
渡辺 芳人, 荘司 長三
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Application no：特願2017-195706 Date applied：2017.10
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シトクロムP450モノオキシゲナーゼデコイ基質
渡辺 芳人、荘司 長三
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Application no：特願2017-173446 Date applied：2017.9
Country of applicant：Domestic
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シトクロムP450モノオキシゲナーゼデコイ基質
渡辺 芳人, 荘司 長三
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Application no：特願2017-173446 Date applied：2017.9
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炭化水素系基質の水酸化のための材料およびその利用
渡辺 芳人、荘司 長三
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Application no：特願2015-201431 Date applied：2015.10
Country of applicant：Domestic
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細菌の増殖抑制
荘司長三、渡辺芳人、白瀧千夏子、岩井佑介
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Applicant：国立大学法人名古屋大学
Application no：特願2014-061575 Date applied：2014.3
Country of applicant：Domestic
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ヘム蛋白質のヘム置換法
渡辺芳人、荘司長三、川上了史
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Applicant：国立大学法人名古屋大学代表者 浜口 道成
Application no：61/610,112 Date applied：2012.3
Country of applicant：Foreign country
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不活性炭化水素の水酸化方法およびダミー分子
荘司長三、川上了史、渡辺芳人
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Applicant：国立大学法人名古屋大学代表者 浜口 道成
Application no：特願2010-164828 Date applied：2010.7
Country of applicant：Domestic
本発明は、シトクロムP450モノオキシゲナーゼとダミー分子とを用いて不活性炭化水素を水酸化する方法、および、この水酸化方法に用いられるダミー分子に関する。
Teaching Experience (On-campus)
Teaching Experience (On-campus) 4
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生物無機化学
2017
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無機・物化機器分析
2017
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化学講究
2017
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基礎セミナー
2016
Teaching Experience (Off-campus)
Teaching Experience (Off-campus) 4
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生物無機化学
（Nagoya University）
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無機・物化機器分析
（Nagoya University）
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基礎セミナー
（Nagoya University）
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化学講究
（Nagoya University）