Production of acetophenone C-glucosides using an engineered C-glycosyltransferase in Escherichia coli. Issue 19 (9th May 2018)

• Record Type: Journal Article
• Authors: Chen, Dawei; Chen, Ridao; Xie, Kebo; Duan, Yangyang; Dai, Jungui
• Is Part Of: Tetrahedron letters. Volume 59:Issue 19(2018)
• Page Start: 1875
• Page End: 1878
• Publication Date: 2018-05-09
• Subjects: C-Glycosyltransferase -- Whole-cell bioconversion -- Mono-C-glucosides -- Bis-C-glucosides -- SGLT2 inhibitors; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.04.006
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An engineered whole-cell bioconversion for large-scale production of C-glucosides was developed. Eight novel acetophenone mono- and bis-C-glucosides were obtained. Mono-C-glucosides exhibited potent inhibitory effects against SGLT2. 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 of4a 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.