Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives.
Efficient and highly regioselective synthesis of the potential 6''-O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved usingCandida antarcticalipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion, and 6''-regioselectivity were as high as 8.65 mM/h, 100%, and 100%, respectively. Kinetic and operational stability investigations evidently demonstrated excellent enzyme compatibility of the 2-MeTHF compared to the traditional organic solvents. With respect to the antioxidant properties, three unsaturated ester derivatives showed slightly lower DPPH radical scavenging activities than the parent agent. Interestingly, further studies also revealed that the antiradical capacities of the acylates decreased with the elongation of the unsaturated aliphatic chain length from C4 to C11. The reason might be attributed to the increased steric hindrance derived from the acyl residues in derivatives.
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Zhaoyu
0000-0002-0803-9319
Z
Wang
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Yanhong
0000-0002-4890-9294
Y
Bi
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Rongling
R
Yang
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Xiangjie
X
Zhao
College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, China.
Ling
L
Jiang
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Chun
C
Zhu
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Yuping
Y
Zhao
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
Jianbo
J
Jia
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