Deracemization of (+/-)-cis-2,3-epoxyheptane via enantioconvergent biocatalytic hydrolysis using Nocardia EH1-epoxide hydrolase

被引：33

作者：

Kroutil, W ^{[1
]}

Mischitz, M ^{[1
]}

Plachota, P ^{[1
]}

Faber, K ^{[1
]}

机构：

[1] GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 46期

关键词：

D O I：

10.1016/0040-4039(96)01935-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biocatalytic hydrolysis of (+/-)-cis-2,3-epoxyheptane using lyophilized bacterial cells of Nocardia EH1 gave (2R,3R)-heptane-2,3-diol as the sole product in 79% yield and 91% e.e. at 100% conversion. The pathway of this deracemization was elucidated by (OH2)-O-18-labelling experiments using a partially purified epoxide hydrolase preparation and was shown to proceed in an enantioconvergent manner. Thus both substrate enantiomers were hydrolyzed via attack of [OH-] at the respective (S)-configurated C-atom with concomitant inversion of configuration. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：8379 / 8382

页数：4

共 8 条

[1] Enantioconvergent transformation of racemic cis-beta-alkyl substituted styrene oxides to (R,R) threo diels by microsomal epoxide hydrolase catalysed hydrolysis [J].