Peroxygenase-Catalysed Sulfoxidations in Non-Aqueous Media
Huanhuan Li (Xi’an Jiaotong University, Chinese Academy of Sciences)
Qianqian Shen (Chinese Academy of Sciences, Xi’an Jiaotong University)
Xiaoying Zhou (Chinese Academy of Sciences)
Peigao Duan (Xi’an Jiaotong University)
F. Hollmann (TU Delft - BT/Biocatalysis)
Yawen Huang (Chinese Academy of Sciences)
Wuyuan Zhang (Chinese Academy of Sciences)
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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.
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