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Biocatalytic Preparation of Chiral Sulfoxides through Asymmetric Reductive Resolution by Methionine Sulfoxide Reductase A
Author(s) -
Peng Liaotian,
Wen Yuanmei,
Chen Yu,
Yuan Zhimei,
Zhou Yang,
Cheng Xiaoling,
Chen Yongzheng,
Yang Jiawei
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800279
Subject(s) - sulfoxide , enantiomeric excess , biocatalysis , substrate (aquarium) , chemistry , msra , enantiomer , enantioselective synthesis , yield (engineering) , organic chemistry , methionine , catalysis , reaction mechanism , amino acid , biochemistry , materials science , oceanography , geology , metallurgy
Here we report an environmentally friendly method for the preparation of chiral sulfoxides under high substrate concentration using recombinant methionine sulfoxide reductase A from Pseudomonas monteilii ( pm MsrA) as a biocatalyst. Our results show that this enzyme can effectively accomplish the preparation of ( R )‐sulfoxides with approximately 50 % yield and 94–99 % enantiomeric excess through asymmetric reductive resolution of racemic sulfoxide. With the establishment of the enzyme regeneration system, the initial substrate concentration could be increased 40–100 times compared to our original report. The ( R )‐sulfoxides were obtained with high enantioselectivity under the substrate concentration up to 200 m m (approximately 32 g L −1 ), representing a quite high substrate concentration in biocatalytic preparation of chiral sulfoxides. Moreover, this system showed fairly good activity and enantioselectivity towards a series of ortho ‐ and para ‐substituted phenyl methyl sulfoxides under high substrate concentration.