Peroxygenase-Catalysed Sulfoxidations in Non-Aqueous Media

Huanhuan Li, Qianqian Shen, Xiaoying Zhou, Peigao Duan*, Frank Hollmann*, Yawen Huang, Wuyuan Zhang*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

Chiral sulfoxides are valuable building blocks in asymmetric synthesis. However, the biocatalytic synthesis of chiral sulfoxides is still challenged by low product titres. Herein, we report the use of peroxygenase as a catalyst for asymmetric sulfoxidation under non-aqueous conditions. Upon covalent immobilisation, the peroxygenase showed stability and activity under neat reaction conditions. A large variety of sulfides was converted into chiral sulfoxides in very high product concentration with moderate to satisfactory optical purity (e. g. 626 mM of (R)-methyl phenyl sulfoxide in approx. 89 % ee in 48 h). Further polishing of the ee value via cascading methionine reductase A (MsrA) gave>99 % ee of the sulfoxide. The robustness of the enzymes and high product titer is superior to the state-of-the-art methodologies. Gram-scale synthesis has been demonstrated. Overall, we demonstrated a practical and facile catalytic method to synthesize chiral sulfoxides.

Original languageEnglish
Article numbere202301321
Number of pages7
JournalChemSusChem
Volume17
Issue number6
DOIs
Publication statusPublished - 2023

Keywords

  • Asymmetric sulfoxidation
  • Biocatalysis
  • Cascade
  • Enzyme Immobilisation
  • Peroxygenase

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