Tetrahedron Letters 2018-04-04

Production of acetophenone C-glucosides using an engineered C-glycosyltransferase in Escherichia coli

Dawei Chen, Ridao Chen, Kebo Xie, Yangyang Duan, Jungui Dai

Index: 10.1016/j.tetlet.2018.04.006

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Abstract

Eight novel acetophenone mono- and bis-C-glucosides were obtained by whole cells harboring an engineered C-glycosyltransferase. Optimization of the fed-bath process improved the yield of 4a to 0.97 mg/mL with 95% conversion rate, which is 2.9-fold higher than that of the single-bath. Four mono-C-glucosides (1a–4a) exhibited potent SGLT2 inhibitory activities with IC50 values at 10−6 M. These findings provide a cost-effective and practical synthetic strategy to produce structurally diverse and novel bioactive C-glucosides for drug discovery.