title: alpha-Glucopyranoimidazolines as intermediate analogue inhibitors of family 20 beta-N-acetylglucosaminidases.
abstract: The alpha-glucopyranoimidazolines, 2-methyl-(1,2-dideoxy-alpha-d-glucopyrano)[2,1-d]-1-imidazolines 1 and 2, have been synthesized and evaluated as inhibitors of beta-N-acetylglucosaminidases (NAGs). Compounds 1 and 2, mimicking the oxazolinium ion intermediate in enzyme catalysis, served as potent and competitive inhibitors of family 20 NAGs with K(i) as low as 0.1 microM, but showed no inhibitory activities toward family 3 NAGs. Due to structural and electrostatic resemblance to the oxazolinium ion intermediate, the alpha-glucopyranoimidazolines may lead to novel and selective inhibitors of mechanistically related glycosidases such as family 18 chitinases.
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Kato
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Uno
authors.forename: Jun
authors.initials: J
authors.lastname: Hiratake
authors.forename: Kanzo
authors.initials: K
authors.lastname: Sakata
mesh_terms: D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D048288:Imidazolines / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
chemical_list: D004791:Enzyme Inhibitors; D048288:Imidazolines; D000118:Acetylglucosaminidase