生物催化
级联
还原(数学)
化学
酶
对映选择合成
组合化学
有机化学
催化作用
数学
离子液体
色谱法
几何学
作者
Jin Tian,Shihuan Zhou,Yanli Chen,Yuyan Zhao,Jintao Wang,Pengyuan Yang,Xianlin Xu,Yongzheng Chen,Xiaoling Cheng,Jiawei Yang
标识
DOI:10.1002/chem.202304081
摘要
Abstract Optically 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.
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