Diversity of sugar acceptor of glycosyltransferase 1 from Bacillus cereus and its application for glucoside synthesis

Applied Microbiology and Biotechnology
Hsi-Ho ChiuYaw-Kuen Li

Abstract

Glycosyltransferase 1 from Bacillus cereus (BcGT1) catalyzes the transfer of a glucosyl moiety from uridine diphosphate glucose (UDP-glucose) to various acceptors; it was expressed and characterized. The specificity of acceptors was found to be broad: more than 20 compounds classified into O-, S-, and N-linkage glucosides can be prepared with BcGT1 catalysis. Based on this work, we conclude that the corresponding acceptors of these compounds must possess the following features: (1) the acceptors must contain at least one aromatic or fused-aromatic or heteroaromatic ring; (2) the reactive hydroxyl or sulfhydryl or amino group can attach either on the aromatic ring or on its aliphatic side chain; and (3) the acceptors can be a primary, secondary, or even a tertiary amine. Four representative acceptors-fluorescein methyl ester, 17-β-estradiol, 7-mercapto-4-methylcoumarin, and 6-benzylaminopurine-were chosen as a candidate acceptor for O-, S-, and N-glucosidation, respectively. These enzymatic products were purified and the structures were confirmed with mass and NMR spectra. As all isolated glucosides are β-anomers, BcGT1 is confirmed to be an inverting enzyme. This study not only demonstrates the substrate promiscuity of BcGT1 bu...Continue Reading

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Citations

Oct 25, 2017·Beilstein Journal of Organic Chemistry·Jihen AtiRichard Daniellou
Mar 12, 2020·Frontiers in Bioengineering and Biotechnology·Luan Luong ChuHanhong Bae
Oct 24, 2018·Journal of Agricultural and Food Chemistry·Fangyu DingBingfang He
Sep 27, 2020·Nature Communications·Manuel Nieto-DomínguezMaría Jesús Martínez

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