title: Efficient synthesis of kinsenoside and goodyeroside a by a chemo-enzymatic approach.
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%.
authors.affiliation: 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. zyhust123@163.com.
authors.forename: Yang
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: 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. missxia55@163.com.
authors.forename: Yihong
authors.initials: Y
authors.lastname: Xia
authors.affiliation: 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. laiyongji1024@163.com.
authors.forename: Yongji
authors.initials: Y
authors.lastname: Lai
authors.affiliation: Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. nagexiaoshui@163.com.
authors.forename: Fang
authors.initials: F
authors.lastname: Tang
authors.affiliation: 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. luozengwei@hust.edu.cn.
authors.forename: Zengwei
authors.initials: Z
authors.lastname: Luo
authors.affiliation: 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. missxia55@163.com.
authors.forename: Yongbo
authors.initials: Y
authors.lastname: Xue
authors.affiliation: 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. gyap@mail.hust.edu.cn.
authors.forename: Guangmin
authors.initials: G
authors.lastname: Yao
authors.affiliation: 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. zyhust123@163.com.
authors.forename: Yonghui
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. tjzhangjinwen@163.com.
authors.forename: Jinwen
authors.initials: J
authors.lastname: Zhang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D005959:Glucosidases / Q000378:metabolism*; D009005:Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C422363:3-glucopyranosyloxybutanolide; C511346:3-hydroxy-gamma-butyrolactone; D005663:Furans; D009005:Monosaccharides; C507480:goodyeroside A; D005959:Glucosidases; D015107:4-Butyrolactone