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Enzymatic Synthesis of Acylphloroglucinol 3‐ C ‐Glucosides from 2‐ O ‐Glucosides using a C ‐Glycosyltransferase from Mangifera indica
Author(s) -
Chen Dawei,
Sun Lili,
Chen Ridao,
Xie Kebo,
Yang Lin,
Dai Jungui
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600411
Subject(s) - regioselectivity , chemistry , glycosyltransferase , stereochemistry , enzyme , mangifera , uridine diphosphate , glucoside , catalysis , organic chemistry , biology , botany , medicine , alternative medicine , pathology
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 indi ca. 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.