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Review
. 2021 Aug 19:9:714899.
doi: 10.3389/fchem.2021.714899. eCollection 2021.

Sulfoxide Reductases and Applications in Biocatalytic Preparation of Chiral Sulfoxides: A Mini-Review

Tao Peng  1 , Xiaoling Cheng  1 , Yongzheng Chen  2 , Jiawei Yang  1   2
Affiliations
Review

Sulfoxide Reductases and Applications in Biocatalytic Preparation of Chiral Sulfoxides: A Mini-Review

Tao Peng et al. Front Chem. .

Abstract

Chiral sulfoxides are valuable organosulfur compounds that have been widely used in medicinal and organic synthesis. Biocatalytic approaches for preparing chiral sulfoxides were developed in the past few years, mainly through asymmetric oxidation of prochiral sulfides. Recently, the application of sulfoxide reductase to prepare chiral sulfoxides through kinetic resolution has emerged as a new method, exhibiting extraordinary catalytic properties. This article reviews the chemical and biological functions of these sulfoxide reductases and highlights their applications in chiral sulfoxide preparation.

Keywords: DMSO reductase; biocatalysis; chiral sulfoxide; kinetic resolution; methionine sulfoxide reductase.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

FIGURE 1
FIGURE 1
Overview of methionine sulfoxide reductase and application in chiral sulfoxides preparation. (A) General catalytic mechanism of methionine sulfoxide reductase. (B) Schematic presentation of kinetic resolution catalyzed by MsrA for (R)-sulfoxides preparation. (C) Schematic presentation of cascade chemoenzymatic reaction for (R)-sulfoxides preparation by MsrA and oxaziridine. (D) Schematic presentation of high-throughput screening strategies of MsrA and the latest achievement in modification of substrate scope. (E) Schematic presentation of kinetic resolution catalyzed by MsrB for (S)-sulfoxides preparation. (F) Summary of Msr enzymes applied for preparation of chiral sulfoxides through kinetic resolution.
FIGURE 2
FIGURE 2
Overview of DMSO reductase and application in chiral sulfoxides preparation. (A) Typical constitution and electron transferring of DMSO reductase in E. coli. (B) Schematic presentation of the proposed catalytic mechanism for the catalytic cycle of DMSO reductase. (C) Representative presentation of DMSO reductases from different organisms shows opposite stereospecificity toward the same substrate. (D) Representative presentation of one DMSO reductase shows opposite stereospecificity toward different substrates.
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