Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

Jian-Dong Zhang; Xiao-Xiao Yang; Qiao Jia; Jian-Wei Zhao; Li-Li Gao; When-Chao Gao; Hong-Hong Chang; Wen-Long Wei; Jian-He Xu

doi:10.1039/C8CY02377H

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Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system†

Jian-Dong Zhang,

*^a Xiao-Xiao Yang,^a Qiao Jia,^a Jian-Wei Zhao,^a Li-Li Gao,^b When-Chao Gao,

^a Hong-Hong Chang,^a Wen-Long Wei^a and Jian-He Xu^c

Author affiliations

* Corresponding authors

^a Department of Biological and Pharmaceutical Engineering, College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan, Shanxi, China
E-mail: zhangjiandong@tyut.edu.cn

^b College of Environmental Science and Engineering, Taiyuan University of Technology, Taiyuan, Shanxi, China

^c Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China

Abstract

A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97–99% ee and 79–99% conversion from readily available racemic epoxides.

This article is part of the themed collection: Asymmetric catalysis

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Article information

DOI: https://doi.org/10.1039/C8CY02377H
Article type: Communication
Submitted: 21 nov 2018
Accepted: 04 dec 2018
First published: 04 dec 2018

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Catal. Sci. Technol., 2019,9, 70-74

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Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

J. Zhang, X. Yang, Q. Jia, J. Zhao, L. Gao, W. Gao, H. Chang, W. Wei and J. Xu, Catal. Sci. Technol., 2019, 9, 70 DOI: 10.1039/C8CY02377H

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Catalysis Science & Technology

Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system†

Abstract

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Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

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