Issue 37, 2016
From the journal:

Chemical Communications

Structure-guided stereoselectivity inversion of a short-chain dehydrogenase/reductase towards halogenated acetophenones†

Aipeng Li,a   Lidan Ye,ab   Xiaohong Yang,a   Chengcheng Yang,a   Jiali Guc  and  Hongwei Yu*a  

* Corresponding authors

a Institute of Bioengineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China
E-mail: yuhongwei@zju.edu.cn

b Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027, P. R. China

c College of Life Science, Department of Materials Chemistry, Huzhou University, Huzhou 313000, P. R. China

Abstract

The structure-guided rational design of an NADH-dependent short-chain dehydrogenase/reductase (SDR) reversed the stereoselectivity towards halogenated acetophenones from Prelog to anti-Prelog. The enzyme–substrate interactions involving an aromatic ring and a halogen atom were proven to play critical roles in determining the stereoselectivity of these ketone reductions besides the steric repulsion.

Graphical abstract: Structure-guided stereoselectivity inversion of a short-chain dehydrogenase/reductase towards halogenated acetophenones

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Article information

DOI
https://doi.org/10.1039/C6CC00051G
Article type
Communication
Submitted
04 Jan 2016
Accepted
11 Apr 2016
First published
11 Apr 2016

Chem. Commun., 2016,52, 6284-6287

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Structure-guided stereoselectivity inversion of a short-chain dehydrogenase/reductase towards halogenated acetophenones

A. Li, L. Ye, X. Yang, C. Yang, J. Gu and H. Yu, Chem. Commun., 2016, 52, 6284 DOI: 10.1039/C6CC00051G

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