Efficient synthesis of kinsenoside and goodyeroside a by a chemo-enzymatic approach

• Published in: Molecules (Basel, Switzerland) Vol. 19; no. 10; pp. 16950 - 16958
• Main Authors: Zhang, Yang, Xia, Yihong, Lai, Yongji, Tang, Fang, Luo, Zengwei, Xue, Yongbo, Yao, Guangmin, Zhang, Yonghui, Zhang, Jinwen
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 22.10.2014; MDPI
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemical synthesis; 4-Butyrolactone - chemistry; Acids; biocatalysis; Catalysis; chemo-enzymatic synthesis; Enzymes; Furans - chemical synthesis; glucosidase; Glucosidases - metabolism; goodyeroside A; Investigations; kinsenoside; Letter; Monosaccharides - chemical synthesis; Solvents; Stereoisomerism; China
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules191016950

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%.