Studies on N-Glycosides

Part 28. The Transglycosidation of N-Glycosides

Abstract

The substitutions of aglycon or sugar-component of the several aromatic N-glycosides by the other amines or sugars in alcoholic and water media have been studied. Boiling p-aminobenzoic acid-N-D-glucoside with p-sulfanilamide in ethanol gave crystals of p-sulfanil-amide-N-D-glucoside. The reverse substitution was proved by means of paper chromato-graphy. In the similar way, the aglycon-substitutions between the N-glucosides of anesthesin and p-sulfanilande, anesthesin and p-aminobenzoic acid, and p-sufanilamide and p-toluidine were investigated. The probable order of the chemical affinities of these aglycons for the substitution are p-toluidine, p-sulfanilamide, anesthesin, and p-aminobenzoic acid. p-Sulfanilamide-N-D-xyloside was substituted by p-glucose to give the N-D-glucoside in the boiling ethanol, and the reverse substitution was proved paper-chromatographically. The aglycon substitutions between the glucosides of p-aminobenzoic acid and p-sulfanilamide in the water medium at pH 6.0 and 30°C, were confirmed by plotting the newly formed N-glucosides at several intervals on the paper chromatograms.