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

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Abstract

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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Acknowledgments

We thank the National Natural Science Foundation of China (31501421, 21102027), Qing Lan Project of Jiangsu Province, Key Research Program of Industry and Information Technology of Huai’an (HAG2015031), Natural Science Foundation of Jiangsu Province (BK2012243), Foundation of Jiangsu Provincial Engineering Laboratory for Biomass Conversion and Process Integration (JPELBCPL2014002), Ordinary University Graduate Students’ Scientific Research Innovation Program of Jiangsu Province (HGYK201403), Foundation of Huaiyin Institute of Technology (HGB1401), and College Students Innovation and Entrepreneurship Training Projects of Jiangsu Province (201511049017Z) for the financial support.

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Authors and Affiliations

  1. School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai’an, 223003, People’s Republic of China

    Zhao-Yu Wang, Wen-Ying Du, Rong-Ling Yang, Yan-Hong Bi, Xiao-Tian Yuan, Yan-Yong Mao, Yu-Ping Zhao, Jie Wu & Jian-Bo Jia

  2. Academy of State Administration of Grain, Beijing, 100037, People’s Republic of China

    Zhang-Qun Duan

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  1. Zhao-Yu Wang
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Wang, ZY., Du, WY., Duan, ZQ. et al. Efficient Regioselective Synthesis of the Crotonyl Polydatin Prodrug by Thermomyces lanuginosus Lipase: a Kinetics Study in Eco-friendly 2-Methyltetrahydrofuran. Appl Biochem Biotechnol 179, 1011–1022 (2016). https://doi.org/10.1007/s12010-016-2047-2

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