Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B

Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic ( rac ) sulfoxides. T...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-04, Vol.21 (16), p.3417-3422
Hauptverfasser: Zhao, Yuyan, Jiang, Xu, Zhou, Shihuan, Tian, Jin, Yang, Piao, Chen, Yanli, Zhang, Quan, Xu, Xianlin, Chen, Yongzheng, Yang, Jiawei
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container_end_page 3422
container_issue 16
container_start_page 3417
container_title Organic & biomolecular chemistry
container_volume 21
creator Zhao, Yuyan
Jiang, Xu
Zhou, Shihuan
Tian, Jin
Yang, Piao
Chen, Yanli
Zhang, Quan
Xu, Xianlin
Chen, Yongzheng
Yang, Jiawei
description Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic ( rac ) sulfoxides. This MsrB homologue, named li MsrB, was identified from Limnohabitans sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the S configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L −1 ). This study presents an efficient route for the enzymatic preparation of ( S )-sulfoxides through kinetic resolution. A range of sulfoxides including aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides in the S configuration were prepared through kinetic resolution catalyzed by a new MsrB enzyme.
doi_str_mv 10.1039/d3ob00402c
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Enantiomers
Homology
Kinetics
Methionine
Methionine Sulfoxide Reductases
Reductases
Stereoisomerism
Substrates
Sulfoxides
Sulfoxides - chemistry
title Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B
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