研究者詳細 - 荘司　長三

論文 - 荘司　長三

分割表示 86 件中 41 - 60 件目／全件表示 >>

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

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