Premium
Identification of an ε‐Keto Ester Reductase for the Efficient Synthesis of an ( R )‐α‐Lipoic Acid Precursor
Author(s) -
Zhang YuJun,
Zhang WenXia,
Zheng GaoWei,
Xu JianHe
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500001
Subject(s) - chemistry , lipoic acid , yield (engineering) , escherichia coli , enantiomeric excess , enantiomer , reductase , bioprocess , boronic acid , biochemistry , organic chemistry , stereochemistry , combinatorial chemistry , enzyme , catalysis , enantioselective synthesis , gene , paleontology , materials science , biology , metallurgy , antioxidant
A novel reductase ( Cp AR2) with unusually high activity toward an ε‐keto ester, ethyl 8‐chloro‐6‐oxooctanoate, was isolated from Candida parapsilosis . The asymmetric reduction of ethyl 8‐chloro‐6‐oxooctanoate using Escherichia coli cells coexpressing Cp AR2 and glucose dehydrogenase genes gave ethyl ( R )‐8‐chloro‐6‐hydroxyoctanoate, a key precursor for the synthesis of ( R )‐α‐lipoic acid, in high space‐time yield (530 g L −1 d −1 ) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10‐L scale. This method provides a greener and more cost‐effective method for the industrial production of ( R )‐α‐lipoic acid.