title: Stability of aminooxy glycosides to glycosidase catalysed hydrolysis.
abstract: The stability of the amino(methoxy) beta-glycosidic bond to glycosidase catalysed hydrolysis is reported. Beta-O-benzyl glucose and beta-O-benzyl galactose are substrates hydrolysed by beta-glucosidase and beta-galactosidase from almonds and Escherichia coli, respectively. However their beta-N-benzyl-(O-methoxy)-glucoside and beta-N-benzyl-(O-methoxy)-galactoside derivatives are competitive inhibitors.
authors.affiliation: School of Pharmacy, University of East Anglia, Norwich Research Park, Norwich, UK.
authors.forename: Amjid
authors.initials: A
authors.lastname: Iqbal
authors.forename: Hicham
authors.initials: H
authors.lastname: Chibli
authors.forename: Chris J
authors.initials: CJ
authors.lastname: Hamilton
mesh_terms: D055162:Biocatalysis; D057075:Enzyme Assays; D004791:Enzyme Inhibitors / Q000737:chemistry; D004926:Escherichia coli / Q000737:chemistry / Q000201:enzymology; D029968:Escherichia coli Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006868:Hydrolysis; D007700:Kinetics; D010940:Plant Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry*; D027861:Prunus / Q000737:chemistry / Q000201:enzymology; D012996:Solutions; D013379:Substrate Specificity; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors / Q000737:chemistry*; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D029968:Escherichia coli Proteins; D006027:Glycosides; D010940:Plant Proteins; D012996:Solutions; D001617:beta-Glucosidase; D001616:beta-Galactosidase
keywords: Aminooxy glycoside; Glycosidase; Inert substrate analogue