D. L. Morgan, A. Neuberger
Feb 1, 1977
Citations
0
Influential Citations
12
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl 2-amino-2-deoxy-α- and β- d -glucofuranosides were isolated from the products of a Fischer glycosidation of 2-amino-2-deoxy- d -glucose. N-Acetylation gave crystalline methyl 2-acetamido-2-deoxy-α- d -glucofuranoside, but the β anomer was syrupy [characterised as the tris(p-nitrobenzoate)]. The furanose structure was confirmed by periodate oxidation. The anomeric methyl 2-acetamido-2-deoxy- d -glucofuranosides were hydrolysed at very similar rates, which were also similar to those for the methyl d -glucofuranosides and about double those for the methyl d -glucopyranosides. Comparison of the acid-catalysed hydrolysis of the methyl 2-amino-2-deoxy- d -glucofuranosides with that of the methyl d -glucofuranosides shows an inhibiting effect of the free amino group similar to that for the corresponding pyranosides. The rates of hydrolysis of the aminodeoxy- and acetamidodeoxyglucofuranosides were greater in deuterium oxide than in water and this, together with the markedly negative entropies of activation, suggests that these compounds are hydrolysed by mechanisms similar to those put forward for the hydrolysis of aldofuranosides.