Peroxygenase-Catalysed Sulfoxidations in Non-Aqueous Media

Peroxygenase-Catalysed Sulfoxidations in Non-Aqueous Media

Li, Huanhuan (Xi’an Jiaotong University; Chinese Academy of Sciences)
Shen, Qianqian (Xi’an Jiaotong University; Chinese Academy of Sciences)
Zhou, Xiaoying (Chinese Academy of Sciences)
Duan, Peigao (Xi’an Jiaotong University)
Hollmann, F. (TU Delft BT/Biocatalysis)
Huang, Yawen (Chinese Academy of Sciences)
Zhang, Wuyuan (Chinese Academy of Sciences)

2023

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.

Asymmetric sulfoxidation
Biocatalysis
Cascade
Enzyme Immobilisation
Peroxygenase

http://resolver.tudelft.nl/uuid:cd33c3c4-60d8-4e12-80f1-fbc67e2c26fa

https://doi.org/10.1002/cssc.202301321

1864-5631

ChemSusChem (Print): chemistry & sustainability, energy & materials

Institutional Repository

journal article

© 2023 Huanhuan Li, Qianqian Shen, Xiaoying Zhou, Peigao Duan, F. Hollmann, Yawen Huang, Wuyuan Zhang