Efficient biocatalysis for the production of enantiopure (S)-epoxides using a styrene monooxygenase (SMO) and Leifsonia alcohol dehydrogenase (LSADH) system

被引：39

作者：

Toda, Hiroshi ^{[1
]}

Imae, Ryouta ^{[1
]}

Itoh, Nobuya ^{[1
]}

机构：

[1] Toyama Prefectural Univ, Biotechnol Res Ctr, Fac Engn, Dept Biotechnol, Imizu, Toyama 9390398, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 22-23期

关键词：

HYDROGEN-TRANSFER BIOREDUCTION; RECOMBINANT ESCHERICHIA-COLI; HIGHLY ENANTIOSELECTIVE EPOXIDATION; ASYMMETRIC EPOXIDATION; IDENTIFICATION; METABOLISM; OXIDE; COMPLEXES; CATALYSIS; EPOXIDES;

D O I：

10.1016/j.tetasy.2012.09.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Herein we report the production of enantiopure epoxides through biocatalysis using recombinant Escherichia coli cells expressing Rhodococcus sp. ST-10 styrene monooxygenase (SMO) and Leifsonia sp. S749 alcohol dehydrogenase (LSADH) genes are described. Rhodococcus sp. ST-10 SMO catalyzed the epoxidation of various alkenes, including styrene derivatives, vinyl pyridines, and linear alkenes, to give (S)-epoxides. NADH was regenerated by the reduction of NAD(+) by LSADH with 2-propanol. The E. coli biocatalyst was used in an aqueous/organic biphasic reaction system and the reaction conditions were optimized. Under the optimized conditions, 170 mM of (S)-styrene oxide was obtained from styrene in the organic phase with excellent enantiomeric excess (99.8%). This biocatalytic process was used to synthesize various (S)-epoxides. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1542 / 1549

页数：8

共 2 条

[1] Cascade biocatalysis for production of enantiopure (S)-2-hydroxybutyric acid using recombinant Escherichia coli with a tunable multi-enzyme-coordinate expression system
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SYSTEMS MICROBIOLOGY AND BIOMANUFACTURING, 2021, 1 (02): : 234 - 244
[2] Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System
Yang, Zeyu
Ye, Wenjie
Xie, Youyu
Liu, Qinghai
Chen, Rong
Wang, Hualei
Wei, Dongzhi
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (06) : 1068 - 1076

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