2018年6月25日
Dual-Functional Small Molecules for Generating an Efficient Cytochrome P450BM3 Peroxygenase
Angewandte Chemie - International Edition
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- 巻
- 57
- 号
- 26
- 開始ページ
- 7628
- 終了ページ
- 7633
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/anie.201801592
- 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.
- ID情報
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- DOI : 10.1002/anie.201801592
- ISSN : 1521-3773
- ISSN : 1433-7851
- SCOPUS ID : 85044510626