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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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2014-10, Vol.19 (10), p.16950-16958
Hauptverfasser: Zhang, Yang, Xia, Yihong, Lai, Yongji, Tang, Fang, Luo, Zengwei, Xue, Yongbo, Yao, Guangmin, Zhang, Yonghui, Zhang, Jinwen
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Sprache:eng
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Zusammenfassung: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%.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules191016950