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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fthindawi:oai:hindawi.com:10.1155/2016/4357052 2023-05-15T13:32:38+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 2016 https://doi.org/10.1155/2016/4357052 en eng BioMed Research International https://doi.org/10.1155/2016/4357052 Copyright © 2016 Zhaoyu Wang et al. Biotechnology Research Article 2016 fthindawi https://doi.org/10.1155/2016/4357052 2019-05-26T07:10:39Z 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. Article in Journal/Newspaper Antarc* Antarctica Hindawi Publishing Corporation BioMed Research International 2016 1 7 |
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Biotechnology 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 |
topic_facet |
Biotechnology |
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. |
format |
Article in Journal/Newspaper |
author |
Zhaoyu Wang Yanhong Bi Rongling Yang Xiangjie Zhao Ling Jiang Chun Zhu Yuping Zhao Jianbo Jia |
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 |
publisher |
BioMed Research International |
publishDate |
2016 |
url |
https://doi.org/10.1155/2016/4357052 |
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Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://doi.org/10.1155/2016/4357052 |
op_rights |
Copyright © 2016 Zhaoyu Wang et al. |
op_doi |
https://doi.org/10.1155/2016/4357052 |
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BioMed Research International |
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2016 |
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1 |
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7 |
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1766028781773914112 |