Chemoenzymatic enantioconvergent hydrolysis of p-nitrostyrene oxide into (R)-p-nitrophenyl glycol by a newly cloned epoxide hydrolase VrEH2 from Vigna radiata

被引：20

作者：

Wu, Yan-Wen ^{[1
]}

Kong, Xu-Dong ^{[1
]}

Zhu, Qing-Qing ^{[1
]}

Fan, Li-Qiang ^{[1
]}

Xu, Jian-He ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Biotechnol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2015年 / 58卷

基金：

中国国家自然科学基金;

关键词：

Vigna radiata epoxide hydrolase; Recombinant expression; Enzymatic property; Enantioconvergency; Chemoenzymatic synthesis; (R)-p-nitrophenyl glycol; RACEMIC STYRENE OXIDE; MICROBIOLOGICAL TRANSFORMATIONS; ASPERGILLUS-NIGER; ESCHERICHIA-COLI; RESOLUTION; CLONING; BIOTRANSFORMATIONS; ALCOHOLS; ENZYME;

D O I：

10.1016/j.catcom.2014.08.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An epoxide hydrolase from Vigna radiata, VrEH2, was successfully cloned and overexpressed in Escherichia coli. Its temperature and pH optima were 30 degrees C and 6.5, respectively. VrEH2 showed an opposite regioselectivity towards (S)- and (R)-para-nitrostyrene oxide (pNSO), which enables it to catalyze the enantioconvergent hydrolysis of rac-pNSO affording (R)-p-nitrophenyl glycol (pNPG). Preparative synthesis of (R)-pNPG from rac-pNSO by a chemoenzymatic enantioconvergent hydrolysis route with one quarter time as using VrEH2 alone, gave (R)-pNPG in 99.0% ee and 71.5% overall yield after recrystallization, indicating the potential of VrEH2 as a promising biocatalyst for the preparation of enantiopure diols in organic synthesis. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：16 / 20

页数：5

共 2 条

[1] Heterologous overexpression of Vigna radiata epoxide hydrolase in Escherichia coli and its catalytic performance in enantioconvergent hydrolysis of p-nitrostyrene oxide into (R)-p-nitrophenyl glycol
Zhu, Qing-Qing
He, Wan-Hong
Kong, Xu-Dong
Fan, Li-Qiang
Zhao, Jian
Li, Su-Xia
Xu, Jian-He
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2014, 98 (01) : 207 - 218
[2] Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger
Nellaiah, H
Morisseau, C
Archelas, A
Furstoss, R
Baratti, JC
BIOTECHNOLOGY AND BIOENGINEERING, 1996, 49 (01) : 70 - 77

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