研究者詳細 - 荘司　長三

論文 - 荘司　長三

分割表示 >> ／全件表示 83 件中 1 - 83 件目

A Heme-Acquisition Protein Reconstructed with a Cobalt 5-Oxaporphyrinium Cation and Its Growth-Inhibition Activity Toward Multidrug-Resistant Pseudomonas aeruginosa

Takiguchi Asahi, Sakakibara Erika, Sugimoto Hiroshi, Shoji Osami, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61 巻 ( 7 ) 2022年2月

The Power of Deception: Using Decoy Molecules to Manipulate P450BM3 Biotransformations

Stanfield Joshua Kyle, Shoji Osami

CHEMISTRY LETTERS 50 巻 ( 12 ) 頁： 2025 - 2031 2021年12月

Exploring hitherto uninvestigated reactions of the fatty acid peroxygenase CYP152A1: catalase reaction and Compound I formation

Onoda Hiroki, Tanaka Shota, Watanabe Yoshihito, Shoji Osami

FARADAY DISCUSSIONS 2021年10月

C9orf72-derived arginine-rich poly-dipeptides impede phase modifiers

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 12 巻 ( 1 ) 2021年9月

Short-lived intermediate in N2O generation by P450 NO reductase captured by time-resolved IR spectroscopy and XFEL crystallography

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 118 巻 ( 21 ) 2021年5月

Influence of Solvents on Catalytic C–H Bond Oxidation by a Copper(II)–Alkylperoxo Complex

Yuri Lee, Bohee Kim, Seonghan Kim, Elvis Wang Hei Ng, Shinya Ariyasu, Osami Shoji, Sungho Yoon, Hajime Hirao, Jaeheung Cho

ACS Catalysis 14 巻 ( 5 ) 頁： 3524 - 3532 2024年2月

Heme-substituted protein assembly bridged by synthetic porphyrin: achieving controlled configuration while maintaining rotational freedom

Hiroaki Inaba, Yuma Shisaka, Shinya Ariyasu, Erika Sakakibara, Garyo Ueda, Yuichiro Aiba, Nobutaka Shimizu, Hiroshi Sugimoto, Osami Shoji

RSC Advances 14 巻 ( 13 ) 頁： 8829 - 8836 2024年

Investigating the applicability of the CYP102A1-decoy-molecule system to other members of the CYP102A subfamily

Joshua Kyle Stanfield, Hiroki Onoda, Shinya Ariyasu, Chie Kasai, Eleanor Mary Burfoot, Hiroshi Sugimoto, Osami Shoji

Journal of Inorganic Biochemistry 245 巻頁： 112235 - 112235 2023年8月

Catalytic Oxidation of Methane by Wild-Type Cytochrome P450BM3 with Chemically Evolved Decoy Molecules

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 頁： 8613 - 8623 2023年6月

Construction of Biocatalysts Using the P450 Scaffold for the Synthesis of Indigo from Indole. 国際誌

Yanqing Li, Yingwu Lin, Fang Wang, Jinghan Wang, Osami Shoji, Jiakun Xu

International journal of molecular sciences 24 巻 ( 3 ) 2023年1月

記述言語：英語掲載種別：研究論文（学術雑誌）

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

PubMed

A Compound I Mimic Reveals the Transient Active Species of a Cytochrome P450 Enzyme: Insight into the Stereoselectivity of P450-Catalysed Oxidations

Kazuto Suzuki, Joshua Kyle Stanfield, Keita Omura, Yuma Shisaka, Shinya Ariyasu, Chie Kasai, Yuichiro Aiba, Hiroshi Sugimoto, Osami Shoji

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2023年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：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.

DOI： 10.1002/anie.202215706

Web of Science

Tetraphenylporphyrin Enters the Ring: First Example of a Complex between Highly Bulky Porphyrins and a Protein. 国際誌

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 23 巻 ( 14 ) 頁： e202200095 2022年7月

記述言語：英語掲載種別：研究論文（学術雑誌）

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.

DOI： 10.1002/cbic.202200095

PubMed

Natural and artificial enzymes and medicinal aspects: general discussion. 国際誌

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 234 巻頁： 367 - 387 2022年5月

Designer Outer Membrane Protein Facilitates Uptake of Decoy Molecules into a Cytochrome P450BM3-Based Whole-Cell Biocatalyst 国際誌

Karasawa Masayuki, Yonemura Kai, Stanfield Joshua Kyle, Suzuki Kazuto, Shoji Osami

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 61 巻 ( 7 ) 頁： e202111612 2022年2月

Heme-containing proteins: Structures, functions, and engineering

Osami Shoji, Yuichiro Aiba, Shinya Ariyasu, Hiroki Onoda

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering 頁： 194 - 214 2022年

Gaseous Alkane Hydroxylation by Deceiving Cytochrome P450BM3 Using Decoy Molecules

Joshua Kyle Stanfield, Osami Shoji

JOURNAL OF THE JAPAN PETROLEUM INSTITUTE 65 巻 ( 3 ) 頁： 79 - 87 2022年

記述言語：英語出版者・発行元：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

Web of Science

TRICKING CYTOCHROME P450BM3: CATALYSIS OF VARIOUS NON-NATIVE SUBSTRATE TRANSFORMATIONS USING DECOY MOLECULES

Joshua K. Stanfield, Kazuto Suzuki, Kai Yonemura, Talita Malewschik, Osami Shoji

QUIMICA NOVA 44 巻 ( 8 ) 頁： 982 - 998 2021年

記述言語：ポルトガル語出版者・発行元：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.

DOI： 10.21577/0100-4042.20170747

Web of Science

Investigation of the Characteristics of NLS-PNA: Influence of NLS Location on Invasion Efficiency 査読有り

Aiba Yuichiro, Urbina Gerardo, Shibata Masanari, Shoji Osami

APPLIED SCIENCES-BASEL 10 巻 ( 23 ) 頁： 8663 2020年12月

Expanding the applicability of cytochrome P450s and other haemoproteins 査読有り

Ariyasu Shinya, Stanfield Joshua Kyle, Aiba Yuichiro, Shoji Osami

CURRENT OPINION IN CHEMICAL BIOLOGY 59 巻頁： 155 - 163 2020年12月

Iron(III) 5,15-Diazaporphyrin Catalysts for the Direct Oxidation of C(sp(3))-H Bonds

Nishimura Tsubasa, Ikeue Takahisa, Shoji Osami, Shinokubo Hiroshi, Miyake Yoshihiro

INORGANIC CHEMISTRY 59 巻 ( 21 ) 頁： 15751 - 15756 2020年11月

Enhanced cis- and enantioselective cyclopropanation of styrene catalysed by cytochrome P450BM3 using decoy molecules 査読有り

Suzuki Kazuto, Shisaka Yuma, Stanfield Joshua Kyle, Watanabe Yoshihito, Shoji Osami

CHEMICAL COMMUNICATIONS 56 巻 ( 75 ) 頁： 11026 - 11029 2020年9月

Systematic Evolution of Decoy Molecules for the Highly Efficient Hydroxylation of Benzene and Small Alkanes Catalyzed by Wild-Type Cytochrome P450BM3 査読有り

Yonemura Kai, Ariyasu Shinya, Stanfield Joshua Kyle, Suzuki Kazuto, Onoda Hiroki, Kasai Chie, Sugimoto Hiroshi, Aiba Yuichiro, Watanabe Yoshihito, Shoji Osami

ACS CATALYSIS 10 巻 ( 16 ) 頁： 9136 - 9144 2020年8月

Control of microenvironment around enzymes by hydrogels 査読有り

Kobayashi Yuichiro, Kohara Kenji, Kiuchi Yusuke, Onoda Hiroki, Shoji Osami, Yamaguchi Hiroyasu

CHEMICAL COMMUNICATIONS 56 巻 ( 49 ) 頁： 6723 - 6726 2020年6月

Crystals in Minutes: Instant On-Site Microcrystallisation of Various Flavours of the CYP102A1 (P450BM3) Haem Domain 査読有り

Stanfield Joshua Kyle, Omura Keita, Matsumoto Ayaka, Kasai Chie, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito, Shoji Osami

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59 巻 ( 19 ) 頁： 7611 - 7618 2020年5月

Kristalle in Minutenschnelle: Sofortige Mikrokristallisation verschiedenster Varianten der CYP102A1‐(P450BM3)‐Hämdomäne

Joshua Kyle Stanfield, Keita Omura, Ayaka Matsumoto, Chie Kasai, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe, Osami Shoji

Angewandte Chemie 132 巻 ( 19 ) 頁： 7681 - 7689 2020年5月

Cationic guanine: positively charged nucleobase with improved DNA affinity inhibits self-duplex formation 査読有り

Hibino Masaki, Aiba Yuichiro, Shoji Osami

CHEMICAL COMMUNICATIONS 56 巻 ( 17 ) 頁： 2546 - 2549 2020年2月

Development of a High-Pressure Reactor Based on Liquid-Flow Pressurisation to Facilitate Enzymatic Hydroxylation of Gaseous Alkanes 査読有り

Ariyasu Shinya, Kodama Yusaku, Kasai Chie, Cong Zhiqi, Stanfield Joshua Kyle, Aiba Yuichiro, Watanabe Yoshihito, Shoji Osami

CHEMCATCHEM 11 巻 ( 19 ) 頁： 4709 - 4714 2019年10月

Hijacking the Heme Acquisition System of Pseudomonas aeruginosa for the Delivery of Phthalocyanine as an Antimicrobial 査読有り

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 14 巻 ( 7 ) 頁： 1637 - 1642 2019年7月

Highly malleable haem-binding site of the haemoprotein HasA permits stable accommodation of bulky tetraphenylporphycenes 査読有り

Sakakibara Erika, Shisaka Yuma, Onoda Hiroki, Koga Daiki, Xu Ning, Ono Toshikazu, Hisaeda Yoshio, Sugimoto Hiroshi, Shiro Yoshitsugu, Watanabe Yoshihito, Shoji Osami

RSC ADVANCES 9 巻 ( 32 ) 頁： 18697 - 18702 2019年6月

The effect of decoy molecules on the activity of the P450Bm3 holoenzyme and a heme domain peroxygenase variant 査読有り

Dezvarei Shaghayegh, Shoji Osami, Watanabe Yoshihito, Bell Stephen G.

CATALYSIS COMMUNICATIONS 124 巻頁： 97 - 102 2019年5月

Hoodwinking Cytochrome P450BM3 into Hydroxylating Non-Native Substrates by Exploiting Its Substrate Misrecognition 査読有り

Shoji Osami, Aiba Yuichiro, Watanabe Yoshihito

ACCOUNTS OF CHEMICAL RESEARCH 52 巻 ( 4 ) 頁： 925 - 934 2019年4月

Frontispiece: Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives 査読有り

Masayuki Karasawa, Joshua Kyle Stanfield, Sota Yanagisawa, Osami Shoji, Yoshihito Watanabe

Angewandte Chemie International Edition 57 巻 ( 38 ) 頁： 12264-12269 2018年9月

Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives

Karasawa Masayuki, Stanfield Joshua Kyle, Yanagisawa Sota, Shoji Osami, Watanabe Yoshihito

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57 巻 ( 38 ) 頁： 12264 - 12269 2018年9月

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 130 巻 ( 38 ) 頁： 12444 - 12449 2018年9月

Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives 査読有り

M. Karasawa, J. K. Stanfield, S. Yanagisawa, O. Shoji, Y. Watanabe

Angew. Chem. Int. Ed. 57 巻頁： 12264-12269 2018年9月

Peptide Nucleic Acid Conjugated with Ruthenium-Complex Stabilizing Double-Duplex Invasion Complex Even under Physiological Conditions 査読有り

Masaki Hibino, Yuichiro Aiba, Yoshihito Watanabe, Osami Shoji

ChemBioChem 19 巻 ( 15 ) 頁： 1601-1604 2018年8月

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 査読有り国際誌

E. Goto, Y. Haga, M. Kubo, T. Itoh, C. Kasai, O. Shoji, K. Yamamoto, C. Matsumura, T. Nakano, H. Inui

Chemosphere 210 巻頁： 376-383 - 383 2018年7月

Dual-Functional Small Molecules for Generating an Efficient Cytochrome P450BM3 Peroxygenase 査読有り

Nana Ma, Zhifeng Chen, Jie Chen, Jingfei Chen, Cong Wang, Haifeng Zhou, Lishan Yao, Osami Shoji, Yoshihito Watanabe, Zhiqi Cong

Angewandte Chemie - International Edition 57 巻 ( 26 ) 頁： 7628 - 7633 2018年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：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.

DOI： 10.1002/anie.201801592

Web of Science

Scopus

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 255 巻頁： . 2018年3月

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 255 巻頁： . 2018年3月

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 255 巻頁： . 2018年3月

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 255 巻頁： . 2018年3月

Efficient hydroxylation of cycloalkanes by co-addition of decoy molecules to variants of the cytochrome P450 CYP102A1 査読有り

S. Dezvarei, H. Onoda, O. Shoji, Y. Watanabe, S. G. Bell

J. Inorg. Biochem. 183 巻頁： 137-145 2018年3月

α-Oxidative decarboxylation of fatty acids catalysed by cytochrome P450 peroxygenases yielding shorter-alkyl-chain fatty acids 査読有り

H. Onoda, O.Shoji, K.Suzuki, H.Sugimoto, Y.Shiro, Y.Watanabe

Catal. Sci. Technol. 8 巻 ( 2 ) 頁： 434 - 442 2018年

Reconstitution of full-length P450BM3 with an artificial metal complex by utilising the transpeptidase Sortase A 査読有り国際誌

Keita Omura, Yuichiro Aiba, Hiroki Onoda, Joshua Kyle Stanfield, Shinya Ariyasu, Hiroshi Sugimoto, Yoshitsugu Shiro, Osami Shoji, Yoshihito Watanabe

Chemical Communications 54 巻 ( 57 ) 頁： 7892-7895 - 7895 2018年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Royal Society of Chemistry ({RSC})

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

Web of Science

PubMed

Structures of the Heme Acquisition Protein HasA with Iron(III)-5,15-Diphenylporphyrin and Derivatives Thereof as an Artificial Prosthetic Group 査読有り

Uehara Hiromu, Shisaka Yuma, Nishimura Tsubasa, Sugimoto Hiroshi, Shiro Yoshitsugu, Miyake Yoshihiro, Shinokubo Hiroshi, Watanabe Yoshihito, Shoji Osami

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56 巻 ( 48 ) 頁： 15279 - 15283 2017年11月

Innenrücktitelbild: Structures of the Heme Acquisition Protein HasA with Iron(III)-5,15-Diphenylporphyrin and Derivatives Thereof as an Artificial Prosthetic Group (Angew. Chem. 48/2017) 査読有り

Hiromu Uehara, Yuma Shisaka, Tsubasa Nishimura, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihiro Miyake, Hiroshi Shinokubo, Yoshihito Watanabe, Osami Shoji

Angewandte Chemie 129 巻 ( 48 ) 頁： 15675 - 15675 2017年11月

Capturing an initial intermediate during the P450nor enzymatic reaction using time-resolved XFEL crystallography and caged-substrate 査読有り

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 8 巻 ( 1 ) 頁： 1585 2017年11月

Inhibiting Aggregation of β-Amyloid by Folded and Unfolded Forms of Fimbrial Protein of Gram-Negative Bacteria 査読有り

K. Yamamoto, M. Oyaizu, T. Takahashi, Y. Watanabe, O. Shoji

Chemistry Select 2 巻 ( 28 ) 頁： 9058-9062 2017年10月

Monooxygenation of Nonnative Substrates Catalyzed by Bacterial Cytochrome P450s Facilitated by Decoy Molecules 査読有り

O. Shoji, Y. Watanabe

Chemistry Letters 46 巻 ( 3 ) 頁： 278-288 2017年3月

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 41 巻 ( 1 ) 頁： 302 - 307 2017年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：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

Web of Science

Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules

Suzuki, K., Stanfield, J.K., Shoji, O., Yanagisawa, S., Sugimoto, H., Shiro, Y., Watanabe, Y.

Catalysis Science and Technology 7 巻 ( 15 ) 頁： 3332 - 3338 2017年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：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

Web of Science

Scopus

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 56 巻 ( 35 ) 頁： 10324 - 10329 2017年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：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.

DOI： 10.1002/anie.201703461

Web of Science

Scopus

A Substrate-Binding-State Mimic of H2O2-Dependent Cytochrome P450 Produced by One-point Mutagenesis and Peroxygenation of Non-native Substrates 査読有り

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. 6 巻頁： 5806-5811 2016年8月

Improved oxidation of aromatic and aliphatic hydrocarbons using rate enhancing variants of P450Bm3 in combination with decoy molecules 査読有り

S. D. Munday, O. Shoji, Y. Watanabe, L. L. Wong, S. G. Bell

Chem. Commun. 52 巻頁： 1036-1039 2016年1月

Acetate anion-triggered peroxygenation of non-native substrates by wild-type cytochrome P450s 査読有り

H. Onoda, O. Shoji, Y. Watanabe

Dalton Trans 44 巻頁： 15316-15323 2015年8月

Highly efficient hydroxylation of gaseous alkanes at reduced temperature catalyzed by cytochrome P450BM3 assisted by decoy molecules 査読有り

N. Kawakami, Z. Cong, O. Shoji, Y. Watanabe

Journal of Porphyrins and Phthalocyanines 19 巻頁： 329-334 2015年3月

Activation of Wild-type Cytochrome P450BM3 by the Next Generation of Decoy Molecules: Enhanced Hydroxylation of Gaseous Alkanes and Crystallographic Evidence 査読有り

Z. Cong, O. Shoji, C. Kasai, N. Kawakami, H. Sugimoto, Y. Shiro, Y. Watanabe

ACS Catalysis 5 巻頁： 150–156 2015年1月

Bringing out the potential of wild-type cytochrome P450s using decoy molecules: Oxygenation of nonnative substrates by bacterial cytochrome P450s 査読有り

O. Shoji, Y. Watanabe

Isr. J. Chem. 55 巻 ( 1 ) 頁： 32–39 2015年1月

GluN2B-Selective N-Methyl-d-aspartate (NMDA) Receptor Antagonists Derived from 3-Benzazepines: Synthesis and Pharmacological Evaluation of Benzo[7]annulen-7-amines 査読有り

A. Benner, A. Bonifazi, C. Shirataki, L. Temme, D. Schepmann, W. Quaglia, O. Shoji, Y. Watanabe, C. Daniliuc, B. Wünsch

ChemMedChem 9 巻 ( 4 ) 頁： 741-751 2014年4月

Inhibition of Heme Uptake in Pseudomonas aeruginosa by its Hemophore (HasAp) Bound to Synthetic Metal Complexes 査読有り

C. Shirataki, O. Shoji, M. Terada, S. Ozaki, H. Sugimoto, Y. Shiro, Y. Watanabe

Angew. Chem. Int. Ed. 53 巻頁： 2862-2866 2014年3月

Peroxygenase reactions catalyzed by cytochromes P450 査読有り

O. Shoji, Y. Watanabe

J. Biol. Inorg. Chem 19 巻 ( 4-5 ) 頁： 529-539 2014年2月

Electronic Control of Discrimination between O2 and CO in Myoglobin Lacking the Distal Histidine Residue 査読有り

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 53 巻頁： 1091–1099 2013年12月

Highly Selective Hydroxylation of Benzene to Phenol by Wild-type Cytochrome P450BM3 Assisted by Decoy Molecules 査読有り

O. Shoji, T. Kunimatsu, N. Kawakami, Y. Watanabe

Angew. Chem. Int. Ed. 52 巻頁： 6606-6610 2013年6月

Direct hydroxylation of primary carbons in small alkanes by wild-type cytochrome P450BM3 containing perfluorocarboxylic acids as decoy molecules 査読有り

N. Kawakami, O. Shoji, Y. Watanabe

Chem. Sci. 4 巻頁： 2344-2348 2013年3月

Chiral-Substrate-Assisted Stereoselective Epoxidation Catalyzed by H2O2-Dependent Cytochrome P450SPα 査読有り

T. Fujishiro, O. Shoji, N. Kawakami, T. Watanabe, H. Sugimoto, Y. Shiro, Y. Watanabe

Chemistry-An Asian Journal 7 巻 ( 10 ) 頁： 2286-2293 2012年10月

Single-step reconstitution of apo-hemoproteins at the disruption stage of Escherichia coli cells 査読有り

N. Kawakami, O. Shoji, Y.Watanabe

ChemBioChem 13 巻 ( 14 ) 頁： 2045-2047 2012年9月

Construction of Biocatalysts Using the Myoglobin Scaffold for the Synthesis of Indigo from Indole 査読有り

J. Xu, O. Shoji, T. Fujishiro, T. Ohki, T. Ueno, Y. Watanabe

Catalysis Science & Technology 2 巻頁： 739-744 2012年4月

Molecular Design of Heme Proteins for Future Application 査読有り

H. Nakajima, O. Shoji, Y. Watanabe

Catalysis Surveys from Asia 15 巻 ( 3 ) 頁： 134-143 2011年6月

記述言語：英語掲載種別：研究論文（学術雑誌）

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.

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 査読有り

T. Fujishiro, O. Shoji, S. Nagano, H. Sugimoto, Y. Shiro, Y. Watanabe

J. Biol. Chem. 286 巻頁： 29941-29950 2011年6月

Use of Perfluoro Carboxylic Acids Trick Cytochrome P450BM3 into Initiating Hydroxylation of Gaseous Alkanes 査読有り

N. Kawakami, O. Shoji, Y. Watanabe

Angew.Chem.Int.Ed 50 巻頁： 5315-5318 2011年4月

Design of H2O2-Dependent Oxidation Catalyzed by Hemoproteins 査読有り

O. Shoji, Y. Watanabe

Metallomics 3 巻頁： 379-388 2011年2月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

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.

Non-covalent modification of the active site of cytochrome P450 for inverting the stereoselectivity of monooxygenation 査読有り

Takashi Fujishiro, Osami Shoji, Yoshihito Watanabe

Tetrahedron Letters 53 巻 ( 3 ) 頁： 395-397 2010年12月

記述言語：英語掲載種別：研究論文（学術雑誌）

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.

Understanding substrate misrecognition of hydrogen peroxide dependent cytochrome P450 from Bacillus subtilis 査読有り

Osami Shoji, Takashi Fujishiro, Shingo Nagano, Shota Tanaka, Takuya Hirose, Yoshitsugu Shiro, Yoshihito Watanabe

J. Biol. Inorg. Chem. 15 巻 ( 8 ) 頁： 1331-1339 2010年8月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

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).

Aromatic C-H bond hydroxylation by P450 peroxygenases: a facile colorimetric assay for monooxygenation activities of enzymes based on Russig's blue formation 査読有り

Osami Shoji, Christian Wiese, Takashi Fujishiro, Chikako Shirataki, Bernhard Wünsch, Yoshihito Watanabe

J. Biol. Inorg. Chem. 15 巻 ( 7 ) 頁： 1109-1115 2010年5月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

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.

Hydrogen Peroxide-Dependent Monooxygenations by Tricking the Substrate Recognition of Cytochrome P450BSb 査読有り

Osami Shoji, Takashi Fujishiro, Hiroshi Nakajima, Misa Kim, Shingo Nagano, Yoshitsugu Shiro, Yoshihito Watanabe

Angew. Chem. Int. Ed. 46 巻 ( 20 ) 頁： 3656-3659 2007年5月

Supramolecular array of imizazolylethynyl-zinc-porphyrin 査読有り

Akiharu Satake, Osami Shoji, Yoshiaki Kobuke

J. Organomet. Chem. 692 巻 ( 1-3 ) 頁： 635-644 2006年8月

Single Molecule Visualization of Coordination Assembled Porphyrin Macrocycles Reinforced with Covalent Linkings 査読有り

Osami Shoji, Hiroyuki Tanaka, Tomoji Kawai, Yoshiaki Kobuke

J. Am. Chem. Soc 127 巻 ( 24 ) 頁： 8598 -8599 2005年5月

Coordination Assembled Rings of Ferrocene-Bridged Trisporphyrin with Flexible Hinge-like Motion: Selective Dimer Ring Formation, its Transformation to Larger Rings, and Vice Versa 査読有り

Osami Shoji, Saori Okada, Akiharu Satake, Yoshiaki Kobuke

J. Am. Chem. Soc 127 巻 ( 7 ) 頁： 2201-2210 2005年2月

Temperature Dependence of Circular Dichroism and Fluorescence Decay of Pyrene Appended to the Side Chains of Poly-L-glutamine 査読有り

Osami Shoji, Daisuke Nakajima, Masahiro Ohkawa, Yoshiki Fujiwara, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira

Macromolecules 36 巻 ( 12 ) 頁： 4557-4566 2003年5月

Side-chain Chromophore Orientation and Excitation Energy Transport in Films Prepared from Poly[N5-(R)- and N5-(S)-1-(1-naphthyl)ethyl-L-glutamines] 査読有り

Osami Shoji, Yachiyo Higashi, Sachie Hishinuma, Masaki Sato, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira

Macromolecules 35 巻 ( 6 ) 頁： 2116-2121 2002年2月

Highly controlled side-chain chromophore orientation in poly[N5-1-(1-pyrenyl)ethyl--glutamines] 査読有り

Osami Shoji, Daisuke Nakajima, Masahiko Annaka, Masako Yoshikuni, Takayuki Nakahira

Polymer 43 巻 ( 5 ) 頁： 1711-1714 2001年11月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

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.

Secondary Structure and Side-Chain Chromophore Orientation in Poly(L-glutamines) Having Pyrene Chromophores in the Side Chains 査読有り

Osami Shoji, Masataka Okumura, Hiromi Kuwata, Takuma Sumida, Ryo Kato, Masahiko Annaka, Masako Yoshikuni, and Takayuki Nakahira

Macromolecules 34 巻 ( 12 ) 頁： 4270-4276 2001年5月

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