Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid...
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| Materiálatiipa: | Artihkal |
| Giella: | English |
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MDPI AG
2014-10-01
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| Ráidu: | Molecules |
| Fáttát: | |
| Liŋkkat: | http://www.mdpi.com/1420-3049/19/10/16950 |
| _version_ | 1828792470830317568 |
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| author | Yang Zhang Yihong Xia Yongji Lai Fang Tang Zengwei Luo Yongbo Xue Guangmin Yao Yonghui Zhang Jinwen Zhang |
| author_facet | Yang Zhang Yihong Xia Yongji Lai Fang Tang Zengwei Luo Yongbo Xue Guangmin Yao Yonghui Zhang Jinwen Zhang |
| author_sort | Yang Zhang |
| collection | DOAJ |
| description | Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. |
| first_indexed | 2024-12-12T03:08:57Z |
| format | Article |
| id | doaj.art-db23c29ba7ad4618922f66f20a1aa78c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T03:08:57Z |
| publishDate | 2014-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-db23c29ba7ad4618922f66f20a1aa78c2022-12-22T00:40:27ZengMDPI AGMolecules1420-30492014-10-011910169501695810.3390/molecules191016950molecules191016950Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic ApproachYang Zhang0Yihong Xia1Yongji Lai2Fang Tang3Zengwei Luo4Yongbo Xue5Guangmin Yao6Yonghui Zhang7Jinwen Zhang8Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaTongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaTongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, ChinaKinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%.http://www.mdpi.com/1420-3049/19/10/16950kinsenosidegoodyeroside Achemo-enzymatic synthesisglucosidasebiocatalysis |
| spellingShingle | Yang Zhang Yihong Xia Yongji Lai Fang Tang Zengwei Luo Yongbo Xue Guangmin Yao Yonghui Zhang Jinwen Zhang Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach Molecules kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis |
| title | Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach |
| title_full | Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach |
| title_fullStr | Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach |
| title_full_unstemmed | Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach |
| title_short | Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach |
| title_sort | efficient synthesis of kinsenoside and goodyeroside a by a chemo enzymatic approach |
| topic | kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis |
| url | http://www.mdpi.com/1420-3049/19/10/16950 |
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