LEAD TETRAACETATE OXIDATION OF OLIGOSACCHARIDES

Abstract

Lead tetraacetate oxidation is shown to be useful for examining some structural features of trisaccharides and higher oligosaccharides. Generally, the oxidations follow a course similar to that found with the corresponding disaccharide. In some oligosaccharides, however, glycol groups which resist oxidation are encountered. Such groups are 2,3-trans glycols of central residues which are linked to adjacent residues by 1,4-glycosidic bonds. The apparent inability to complex with lead tetraacetate suggests a conformation for these sugar residues in acetic acid solution which differs from that of the corresponding monosaccharide glycopyranoside. Lead tetraacetate oxidation of oligosaccharides in which central residues are unaffected by the reagent constitutes a unique stepwise degradation of these compounds, and possible applications of the reaction are suggested.