title: Efficient Regioselective Synthesis of the Crotonyl Polydatin Prodrug by Thermomyces lanuginosus Lipase: a Kinetics Study in Eco-friendly 2-Methyltetrahydrofuran.
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.
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China. biowzy@126.com.
authors.forename: Zhao-Yu
authors.initials: ZY
authors.lastname: Wang
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Wen-Ying
authors.initials: WY
authors.lastname: Du
authors.affiliation: Academy of State Administration of Grain, Beijing, 100037, People's Republic of China.
authors.forename: Zhang-Qun
authors.initials: ZQ
authors.lastname: Duan
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Rong-Ling
authors.initials: RL
authors.lastname: Yang
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Yan-Hong
authors.initials: YH
authors.lastname: Bi
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Xiao-Tian
authors.initials: XT
authors.lastname: Yuan
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Yan-Yong
authors.initials: YY
authors.lastname: Mao
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Yu-Ping
authors.initials: YP
authors.lastname: Zhao
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
authors.affiliation: School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors.forename: Jian-Bo
authors.initials: JB
authors.lastname: Jia
mesh_terms: D000215:Acylation; D002384:Catalysis; D032641:Eurotiales / Q000201:enzymology*; D005663:Furans / Q000737:chemistry*; D005960:Glucosides / Q000096:biosynthesis* / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000096:biosynthesis* / Q000737:chemistry; D011355:Prodrugs / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry; D013379:Substrate Specificity
chemical_list: D005663:Furans; D005960:Glucosides; D011355:Prodrugs; D012997:Solvents; D013267:Stilbenes; D008049:Lipase; C550584:2-methyltetrahydrofuran; C058229:polydatin
keywords: 2-Methyltetrahydrofuran; 6″-O-Crotonyl-polydatin; Enzymatic acylation; Polydatin; Thermomyces lanuginosus lipase