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

Molecules

Yongji Lai¹  Yonghui Zhang¹  Yang Zhang¹  Yihong Xia¹  Zengwei Luo¹  Yongbo Xue¹  Guangmin Yao¹  Fang Tang²  Jinwen Zhang² 

[1] 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;Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China;

关键词: kinsenoside;    goodyeroside A;    chemo-enzymatic synthesis;    glucosidase;    biocatalysis;   

DOI  :  10.3390/molecules191016950

来源: DOAJ

【 摘 要 】

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 usingβ-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%.

【 授权许可】

Unknown