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 using Candida antarctica lipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion,...
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ftciteseerx:oai:CiteSeerX.psu:10.1.1.1077.402 2023-05-15T14:03:51+02:00 Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives Zhaoyu Wang Yanhong Bi Rongling Yang Xiangjie Zhao Ling Jiang Chun Zhu Yuping Zhao Jianbo Jia The Pennsylvania State University CiteSeerX Archives application/pdf http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1077.402 http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf en eng http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1077.402 http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf Metadata may be used without restrictions as long as the oai identifier remains attached to it. http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf text ftciteseerx 2020-05-03T00:16:13Z Efficient and highly regioselective synthesis of the potential 6 -O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using Candida antarctica lipase 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. Text Antarc* Antarctica Unknown |
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description |
Efficient and highly regioselective synthesis of the potential 6 -O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using Candida antarctica lipase 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. |
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The Pennsylvania State University CiteSeerX Archives |
format |
Text |
author |
Zhaoyu Wang Yanhong Bi Rongling Yang Xiangjie Zhao Ling Jiang Chun Zhu Yuping Zhao Jianbo Jia |
spellingShingle |
Zhaoyu Wang Yanhong Bi Rongling Yang Xiangjie Zhao Ling Jiang Chun Zhu Yuping Zhao Jianbo Jia Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
author_facet |
Zhaoyu Wang Yanhong Bi Rongling Yang Xiangjie Zhao Ling Jiang Chun Zhu Yuping Zhao Jianbo Jia |
author_sort |
Zhaoyu Wang |
title |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_short |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_full |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_fullStr |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_full_unstemmed |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_sort |
enzymatic synthesis of sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran and antiradical activity of the unsaturated acylated derivatives |
url |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1077.402 http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf |
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Antarc* Antarctica |
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http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf |
op_relation |
http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.1077.402 http://downloads.hindawi.com/journals/bmri/2016/4357052.pdf |
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Metadata may be used without restrictions as long as the oai identifier remains attached to it. |
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