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

Molecules

Yang Zhang²  Yihong Xia²  Yongji Lai²  Fang Tang¹  Zengwei Luo²  Yongbo Xue²  Guangmin Yao²  Yonghui Zhang²  Jinwen Zhang¹ 

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

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

DOI  :  10.3390/molecules191016950

来源: mdpi

【 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 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%.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.