Affiliation:
1. Department of Biochemistry Zunyi Medical University No.6 West Xuefu Road, Xinpu District Zunyi City Guizhou Province P. R. China
2. Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province Zunyi Medical University No.6 West Xuefu Road, Xinpu District Zunyi City Guizhou Province P. R. China
Abstract
AbstractOptically pure sulfoxides are valuable organosulfur compounds extensively employed in medicinal and organic synthesis. In this study, we present a biocatalytic oxidation‐reduction cascade system designed for the preparation of enantiopure sulfoxides. The system involves the cooperation of a low‐enantioselective chimeric oxidase SMO (styrene monooxygenase) with a high‐enantioselective reductase MsrA (methionine sulfoxide reductase A), facilitating “non‐selective oxidation and selective reduction” cycles for prochiral sulfide oxidation. The regeneration of requisite cofactors for MsrA and SMO was achieved via a cascade catalysis process involving three auxiliary enzymes, sustained by cost‐effective D‐glucose. Under the optimal reaction conditions, a series of heteroaryl alkyl, aryl alkyl and dialkyl sulfoxides in R configuration were synthesized through this “one‐pot, one step” cascade reaction. The obtained compounds exhibited high yields of >90 % and demonstrated enantiomeric excess (ee) values exceeding 90 %. This study represents an unconventional and efficient biocatalytic way in utilizing the low‐enantioselective oxidase for the synthesis of enantiopure sulfoxides.
Funder
National Natural Science Foundation of China
Guizhou Provincial Science and Technology Department
Cited by
1 articles.
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