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Molecules 2014, 19(10), 16950-16958; doi:10.3390/molecules191016950

Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach

1
Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China
2
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 24 September 2014 / Revised: 12 October 2014 / Accepted: 15 October 2014 / Published: 22 October 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

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%. View Full-Text
Keywords: kinsenoside; goodyeroside A; chemo-enzymatic synthesis; glucosidase; biocatalysis kinsenoside; goodyeroside A; chemo-enzymatic synthesis; glucosidase; biocatalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Zhang, Y.; Xia, Y.; Lai, Y.; Tang, F.; Luo, Z.; Xue, Y.; Yao, G.; Zhang, Y.; Zhang, J. Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach. Molecules 2014, 19, 16950-16958.

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