title: Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica.
abstract: A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5'-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing, 100050, P.R. China.
authors.forename: Dawei
authors.initials: D
authors.lastname: Chen
authors.affiliation: College of Life and Environmental Sciences, Minzu University of China, 27 Zhong Guan Cun Southern Street, Beijing, 100081, P.R. China.
authors.forename: Lili
authors.initials: L
authors.lastname: Sun
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing, 100050, P.R. China.
authors.forename: Ridao
authors.initials: R
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing, 100050, P.R. China.
authors.forename: Kebo
authors.initials: K
authors.lastname: Xie
authors.affiliation: College of Life and Environmental Sciences, Minzu University of China, 27 Zhong Guan Cun Southern Street, Beijing, 100081, P.R. China.
authors.forename: Lin
authors.initials: L
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xian Nong Tan Street, Beijing, 100050, P.R. China. jgdai@imm.ac.cn.
authors.forename: Jungui
authors.initials: J
authors.lastname: Dai
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry* / Q000378:metabolism; D031022:Mangifera / Q000737:chemistry* / Q000201:enzymology* / Q000378:metabolism; D015394:Molecular Structure
chemical_list: D005960:Glucosides; D006027:Glycosides; D016695:Glycosyltransferases
keywords: C-glycosides; enzyme catalysis; glycosylation; regioselectivity; transferases