title: Anticapsin, an active-site directed irreversible inhibitor of glucosamine-6-phosphate synthetase from Escherichia coli.
abstract: Glucosamine-6-phosphate synthetase from Escherichia coli K-12 is progressively inactivated L-beta-(2,3-epoxycyclohexyl-4-on)alanine (anticapsin). With increasing concentrations of anticapsin the reaction exhibits rate saturation: the minimum inactivation half-time is 1.15 minutes, with a Kin alpha ct of 2.5 microM. Glutamine and competitive inhibitors protect against inactivation. Fructose-6-phosphate promotes the inactivation rate. It is concluded that anticapsin is an active-site directed glutamine analog in the reaction catalyzed by glucosamine-6-phosphate synthetase.
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000494:pharmacology; D001665:Binding Sites; D002238:Carbohydrate Epimerases / Q000037:antagonists & inhibitors*; D004926:Escherichia coli / Q000201:enzymology*; D005944:Glucosamine / Q000031:analogs & derivatives / Q000096:biosynthesis; D019298:Glucose-6-Phosphate / Q000031:analogs & derivatives*; D005958:Glucosephosphates / Q000096:biosynthesis; D005973:Glutamine / Q000494:pharmacology; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing) / Q000037:antagonists & inhibitors*; D007700:Kinetics
chemical_list: D005958:Glucosephosphates; D005973:Glutamine; C001293:glucosamine 6-phosphate; D019298:Glucose-6-Phosphate; C000097:anticapsin; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing); D002238:Carbohydrate Epimerases; D005944:Glucosamine; D000409:Alanine