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Probing the Catalytic Promiscuity of a Regio‐ and Stereospecific C‐Glycosyltransferase from Mangifera indica
Author(s) -
Chen Dawei,
Chen Ridao,
Wang Ruishan,
Li Jianhua,
Xie Kebo,
Bian Chuancai,
Sun Lili,
Zhang Xiaolin,
Liu Jimei,
Yang Lin,
Ye Fei,
Yu Xiaoming,
Dai Jungui
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506505
Subject(s) - stereospecificity , mangiferin , glycosylation , glycosyltransferase , chemistry , mangifera , glycoside , stereochemistry , benzophenone , aryl , naringin , biochemistry , enzyme , catalysis , organic chemistry , biology , botany , alkyl , chromatography
The catalytic promiscuity of the novel benzophenone C‐glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica , was explored. MiCGT exhibited a robust capability to regio‐ and stereospecific C‐glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP‐glucose, and also formed O‐ and N‐glycosides. Moreover, MiCGT was able to generate C‐xylosides with UDP‐xylose. The OGT‐reversibility of MiCGT was also exploited to generate C‐glucosides with simple sugar donor. Three aryl‐C‐glycosides exhibited potent SGLT2 inhibitory activities with IC 50 values of 2.6×, 7.6×, and 7.6×10 −7 M , respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C‐glycosidation of bioactive natural and unnatural products in drug discovery.