Probing the Catalytic Promiscuity of a Regio‐ and Stereospecific C‐Glycosyltransferase from Mangifera indica. Issue 43 (1st September 2015)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 43(2015)
• Page Start: 12678
• Page End: 12682
• Publication Date: 2015-09-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201506505
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The catalytic promiscuity of the novel benzophenone C‐glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from <italic>Mangifera indica</italic>, 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 IC₅₀ values of 2.6×, 7.6×, and 7.6×10⁻⁷ <sc>M</sc>, 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.</p> </abstract>