文献类型：期刊文献

英文题名：Toward an environmentally friendly synthesis of chiral γ-lactones: A biocatalytically oxidative desymmetrization pathway

作者：Huang, Qi-Kang[1];Zhang, Yi-Ke[1];Huang, Shou-Cheng[1];Wang, Long-Xing[1];Geng, Qiang[1];Liu, Feng[1];Xu, Jian-He[1];Yu, Hui-Lei[1]

机构：[1]East China Univ Sci & Technol, Shanghai Collaborat Innovat Ctr Biomfg, State Key Lab Bioreactor Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2024

卷号：567

外文期刊名：MOLECULAR CATALYSIS

收录：;EI(收录号：20243316861546);WOS:【SCI-EXPANDED(收录号:WOS:001294922000001)】；

基金：This work was financially supported by the National Key Research and Development Program of China (2021YFC2102900) , the National Natural Science Foundation of China (NO 32271540) , the Shanghai Commission of Science and Technology (23HC1400200), and the Program of Shanghai Academic Research Leader (21XD1400800).

语种：英文

外文关键词：gamma-lactone; Desymmetrization; Biocatalysis

摘要：The direct use of oxygen for the enantioselective Baeyer-Villiger oxidation of cyclobutanone represents a promising, environmentally benign method of generating substituted chiral gamma-lactones, a recurrent motif in natural product skeletons. We herein demonstrate a highly efficient process for the desymmetrization of cyclobutanones by a Baeyer-Villiger monooxygenase that originated from Acinetobacter radioresistens (ArBVMO). By coupling a formate dehydrogenase to the monooxygenase, the reaction can readily be performed at high substrate loading (200 mM) in buffer/toluene biphasic systems. Scaling up the reaction led to bioconversion with a space-time yield of up to 115 g L-1 day(-1), and perfect enantioselectivity (> 99% ee ). The discovery of ArBVMO provides a practical synthetic route to gamma-lactones, overcoming the problems of poor accessibility and the high cost of waste disposal incurred by previous methodologies.