Synlett 2024; 35(05): 552-564
DOI: 10.1055/a-2043-4479
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Biomimetic Synthesis

New Paradigms in Catalysis Inspired by Cytochromes P450

Yanqun Gao‡
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Lu Cheng‡
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Wei Shi
b   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry & Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Yuejun Ouyang
b   Hunan Engineering Research Center for Recycled Aluminum, College of Chemistry & Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Wei Han  ∗
a   Jiangsu Key Laboratory of Biofunctional Materials, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
› Author AffiliationsThis work was sponsored by the Natural Science Foundation of Hunan Province (2020JJ4487 and 2021JJ40431), the Natural Science Foundation of China (21776139), the ‘Qing Lan Project’ Young and Middle-Aged Academic Leaders of Jiangsu Provincial Colleges and Universities, and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
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Abstract

Cytochromes P450 (P450s or CYPs) are versatile biocatalysts capable of realizing a broad range of synthetically challenging reactions. The development of synthetic catalysts/catalytic systems that model enzyme functions is a goal that has long been pursued. In this account, we mainly summarize our latest advances in the field of catalysis inspired by cytochromes P450, including reductive activation strategies for highly efficient oxidations and an unusual l-cystine-derived ligand as a model of P450s for highly efficient iron-catalyzed undirected arene C–H hydroxylation. These new paradigms highlight some of the catalytic properties of P450s, such as effective late-stage functionalization of complex targets, good reactive functional group tolerance, and high catalytic efficiency and selectivity.

1 Introduction

2 Reductive Activation Strategies for Oxygenation

3 An Fe/Cysteine-Based Ligand as a Biomimetic Model of Cytochromes P450 for Arene C–H Hydroxylation

4 Conclusion

Key words

cytochromes P450 - bio-inspired catalysis - iron catalysis - oxidation - late-stage functionalization - reductive activation strategy - I-cystine-derived ligand


Publication History

Received: 30 December 2022

Accepted after revision: 27 February 2023

Accepted Manuscript online:
27 February 2023

Article published online:
27 March 2023

© 2023. Thieme. All rights reserved

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