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Enzymatic Synthesis of Acylphloroglucinol 3‐C‐Glucosides from 2‐O‐Glucosides using a C‐Glycosyltransferase from Mangifera indica |
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| Authors: | Dawei Chen Lili Sun Dr. Ridao Chen Dr. Kebo Xie Prof. Dr. Lin Yang Prof. Dr. Jungui Dai |
| Affiliation: | 1. 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, Beijing, P.R. China;2. College of Life and Environmental Sciences, Minzu University of China, Beijing, P.R. China |
| 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. |
| Keywords: | C-glycosides enzyme catalysis glycosylation regioselectivity transferases |