Biocatalytic C-Glucosylation of Coumarins Using an Engineered C-Glycosyltransferase

Organic Letters
Dawei ChenJungui Dai

Abstract

The enzymatic synthesis of coumarin C-glucosides by an engineered C-glycosyltransferase, MiCGTb-GAGM, was explored in vitro and in vivo. MiCGTb-GAGM exhibited a robust C-glucosylation capability toward structurally diverse coumarin derivatives. The whole-cell bioconversion of MiCGTb-GAGM was exploited for large-scale production of coumarin C-glucosides. Two C-glucosides exhibited potent SGLT2 inhibitory activities with IC50 values at 10-6 M. These findings provide cost-effective and practical synthetic strategies to generate structurally diverse and novel bioactive coumarin C-glycosides for drug discovery.

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