title: Glucosylation of acetic acid by sucrose phosphorylase.
abstract: Transglucosylation from sucrose to acetic acid by sucrose phosphorylase (EC 2.4.1.7) was studied. 1-O-Acetyl-alpha-D-glucopyranose was isolated as the main product of the enzyme reaction. We also compared the pH-dependence of transglycosylation catalyzed by sucrose phosphorylase toward carboxyl and hydroxyl groups. With hydroquinone as an acceptor molecule, the transfer ratio of glucose residue was higher at neutral pH. This pH-activity profile was similar to that of the phosphorolysis of sucrose by sucrose phosphorylase, but with acetic acid as an acceptor molecule, the transfer ratio of glucose residue was higher at low pH. These findings suggest that the undissociated carboxyl group is essential to the acceptor molecule for the transglycosylation reaction of sucrose phosphorylase. In a sensory test, the sour taste of acetic acid was markedly reduced by glucosylation. The threshold value of the sour taste of acetic acid glucosides was approximately 100 times greater than that of acetic acid.
authors.affiliation: Biochemical Research Laboratory, Ezaki Glico Co., Ltd., Osaka, Japan. nomura-koji@glico.co.jp
authors.forename: Koji
authors.initials: K
authors.lastname: Nomura
authors.forename: Kazuhisa
authors.initials: K
authors.lastname: Sugimoto
authors.forename: Hiromi
authors.initials: H
authors.lastname: Nishiura
authors.forename: Kohji
authors.initials: K
authors.lastname: Ohdan
authors.forename: Takahisa
authors.initials: T
authors.lastname: Nishimura
authors.forename: Hideo
authors.initials: H
authors.lastname: Hayashi
authors.forename: Takashi
authors.initials: T
authors.lastname: Kuriki
mesh_terms: D019342:Acetic Acid / Q000378:metabolism*; D001426:Bacterial Proteins / Q000302:isolation & purification / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004926:Escherichia coli / Q000201:enzymology; D029968:Escherichia coli Proteins / Q000302:isolation & purification / Q000378:metabolism; D005964:Glucosyltransferases / Q000302:isolation & purification / Q000378:metabolism*; D006031:Glycosylation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013295:Streptococcus mutans / Q000201:enzymology
chemical_list: D001426:Bacterial Proteins; D029968:Escherichia coli Proteins; D005964:Glucosyltransferases; C025901:sucrose phosphorylase; D019342:Acetic Acid