Preparation and study of a fluorescent sugar analog competitive inhibitor of yeast hexokinase.
The preparation of 2-deoxy-2-amino-N-(5-dimethylamino-1-naphthalene sulfonyl)-glucose (III) designed as a fluorescent competitive inhibitor of hexokinase was achieved after reacting 2-deoxy-2-aminoglucose and 1-dimethylamino-5-naphthalene sulfonyl chloride. (III) showed fluorescence excitation and emission maxima in water at 330 and 507 nm, respectively. (III) was found to competitively inhibit hexokinase and a value of Ki = 3.0 x 10(-3)M was obtained for the system hexokinase B + Mg.ATP + glucose at pH 8.4.
D001665:Binding Sites; D001667:Binding, Competitive; D003619:Dansyl Compounds / Q000494:pharmacology; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000494:pharmacology; D005947:Glucose / Q000494:pharmacology; D006593:Hexokinase / Q000037:antagonists & inhibitors*; D007700:Kinetics; D046911:Macromolecular Substances; D009282:Naphthalenesulfonates / Q000138:chemical synthesis; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013050:Spectrometry, Fluorescence
D003619:Dansyl Compounds; D046911:Macromolecular Substances; D009282:Naphthalenesulfonates; D006593:Hexokinase; D005947:Glucose; D005944:Glucosamine