Unimolecular, bimolecular and intramolecular hydrolysis mechanisms of 4-nitrophenyl β-D-glucopyranoside

Abstract

1,2- trans -Glycosides hydrolyze through different mechanisms at different pH values, but systematic studies are lacking. Here we report the pH-rate constant profile for the hydrolysis of 4-nitrophenyl β-D-glucoside. An inverse kinetic isotope effect of k (H 3 O + )/ k (D 3 O) + = 0.65 in the acidic region indicates that the mechanism requires the formation of the conjugate acid of the substrate for the reac..