Efficient Regioselective Synthesis of the Crotonyl Polydatin Prodrug by Thermomyces lanuginosus Lipase: a Kinetics Study in Eco-friendly 2-Methyltetrahydrofuran

Applied Biochemistry and Biotechnology - Tập 179 - Trang 1011-1022 - 2016
Zhao-Yu Wang1, Wen-Ying Du1, Zhang-Qun Duan2, Rong-Ling Yang1, Yan-Hong Bi1, Xiao-Tian Yuan1, Yan-Yong Mao1, Yu-Ping Zhao1, Jie Wu1, Jian-Bo Jia1
1School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai’an, People’s Republic of China
2Academy of State Administration of Grain, Beijing, People’s Republic of China

Tóm tắt

Bio-based solvents have recently been discussed as sustainable green and promising alternatives to conventional organic media for enzymatic processes. In this paper, highly regioselective synthesis of the 6″-O-crotonyl-polydatin catalyzed by Thermomyces lanuginosus lipase (TLL) in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was successfully performed for the first time. The results indicated that TLL lipase displayed significantly improved catalytic performance in 2-MeTHF than in other traditional solvents. Under the optimal conditions, the initial reaction rate, 6″-regioselectivity, and maximum substrate conversion were as high as 12.38 mM h−1, 100 %, and 100 %, respectively. Moreover, further investigations on the operational stability, kinetic parameters like V max, K m, V max/K m, and E a revealed that 2-MeTHF exhibited excellent biocompatibility and rendered the greener process of the enzymatic acylation.

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