Reaction engineering blocks ether cleavage for synthesizing chiral cyclic hemiacetals catalyzed by unspecific peroxygenase

Xiaofeng Han, Fuqiang Chen, Huanhuan Li, Ran Ge, Qianqian Shen, Peigao Duan (), Xiang Sheng () and Wuyuan Zhang ()
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Xiaofeng Han: Inner Mongolia Minzu University
Fuqiang Chen: Chinese Academy of Sciences
Huanhuan Li: Chinese Academy of Sciences
Ran Ge: Chinese Academy of Sciences
Qianqian Shen: Chinese Academy of Sciences
Peigao Duan: Xi’an Jiaotong University
Xiang Sheng: Chinese Academy of Sciences
Wuyuan Zhang: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Hemiacetal compounds are valuable building blocks in synthetic chemistry, but their enzymatic synthesis is limited and often hindered by the instability of hemiacetals in aqueous environments. Here, we show that this challenge can be addressed through reaction engineering by using immobilized peroxygenase from Agrocybe aegerita (AaeUPO) under neat reaction conditions, which allows for the selective C-H bond oxyfunctionalization of environmentally significant cyclic ethers to cyclic hemiacetals. A wide range of chiral cyclic hemiacetal products are prepared in >99% enantiomeric excess and 95170 turnover numbers of AaeUPO. Furthermore, by changing the reaction medium from pure organic solvent to alkaline aqueous conditions, cyclic hemiacetals are in situ transformed into lactones. Lactams are obtained under the applied conditions, albeit with low enzyme activity. These findings showcase the synthetic potential of AaeUPO and offer a practical enzymatic approach to produce chiral cyclic hemiacetals through C-H oxyfunctionalization under mild conditions.

Date: 2024
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DOI: 10.1038/s41467-024-45545-z

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