title: Diversity of sugar acceptor of glycosyltransferase 1 from Bacillus cereus and its application for glucoside synthesis.
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 but also showed the great application prospect of this enzyme in bioconversion of valuable bioactive molecules.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Hsi-Ho
authors.initials: HH
authors.lastname: Chiu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Mo-Yuan
authors.initials: MY
authors.lastname: Shen
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Yuan-Ting
authors.initials: YT
authors.lastname: Liu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Yu-Lieh
authors.initials: YL
authors.lastname: Fu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Yu-An
authors.initials: YA
authors.lastname: Chiu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan.
authors.forename: Ya-Huei
authors.initials: YH
authors.lastname: Chen
authors.affiliation: Industrial Technology Research Institute, 195, Sec. 4, Chung Hsing Rd., Chutung, Hsinchu, 31040, Taiwan.
authors.forename: Chin-Ping
authors.initials: CP
authors.lastname: Huang
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Science Building 2, 1001 Ta Hsueh Road, Hsinchu, 30010, Taiwan. ykl@faculty.nctu.edu.tw.
authors.forename: Yaw-Kuen
authors.identifier: http://orcid.org/0000-0002-6097-7484
authors.initials: YK
authors.lastname: Li
mesh_terms: D001409:Bacillus cereus / Q000201:enzymology* / Q000235:genetics; D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D001593:Benzyl Compounds / Q000378:metabolism; D003374:Coumarins / Q000378:metabolism; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D004958:Estradiol / Q000378:metabolism; D005960:Glucosides / Q000378:metabolism*; D016695:Glycosyltransferases / Q000235:genetics / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D011687:Purines / Q000378:metabolism; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism; D013379:Substrate Specificity; D014532:Uridine Diphosphate Glucose / Q000378:metabolism
chemical_list: C573196:7-mercapto-4-methylcoumarin; D001426:Bacterial Proteins; D001593:Benzyl Compounds; D003374:Coumarins; D005960:Glucosides; D011687:Purines; D011994:Recombinant Proteins; D004958:Estradiol; D016695:Glycosyltransferases; C480551:benzylaminopurine; D014532:Uridine Diphosphate Glucose
keywords: BcGT1; Glucosyltransferase; N-glucoside; O-glucoside; S-glucoside