Specific conversion of D-galactose into D-galacturonic acid residues in glycoproteins: a facile method for...

The terminal D-galactopyranosyl residues of asialoglycopeptides isolated from human alpha1-acid glycoprotein were oxidized in nearly quantitative yield to the corresponding uronic acid residues by a two-step sequence employing D-galactose oxidase followed by treatment with Tollens reagent, Ag(NH3)+2. Mild acid hydrolysis of the oxidized glycopeptides led to the isolation of the corresponding aldobiuronic acid(s). Structural and colorimetric analysis revealed that only one aldobiuronic acid 2-amino-2-deoxy-4-O-(beta-D-galactopyranosyluronic acid)-D-glucose, was isolated from the oxidized glycopeptides of alpha1-acid glycoprotein. This method can readily distinguish between the (1 leads to 3), (1 leads to 4), and (1 leads to 6) isomers of the corresponding aldobiuronic acids.