Biocatalytic Preparation of Chiral Sulfoxides through Asymmetric Reductive Resolution by Methionine Sulfoxide Reductase A. Issue 15 (28th May 2018)

• Record Type: Journal Article
• Authors: Peng, Liaotian; Wen, Yuanmei; Chen, Yu; Yuan, Zhimei; Zhou, Yang; Cheng, Xiaoling; Chen, Yongzheng; Yang, Jiawei
• Is Part Of: ChemCatChem. Volume 10:Issue 15(2018)
• Page Start: 3284
• Page End: 3290
• Publication Date: 2018-05-28
• Subjects: sulfoxides -- biocatalysis -- chiral resolution -- reduction -- methionine sulfoxide reductase A; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201800279
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: 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 mm (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. Abstract : Turn on chirality : After establishing an enzyme regeneration system, the crude pm MsrA–dithiothreitol preparation effectively accomplishes the preparation of ( R )‐1 a –1 g with 43–46 % yield and 94–99 % ee through asymmetric reductive resolution of racemic sulfoxide even at high substrate concentration.