NOVEL DECOMPOSITION OF AMADORI COMPOUND CATALYZED BY COPPER-ION

A novel decomposition of Amadori compound from glucose catalyzed by copper ion is discussed. The Amadori compounds prepared from glycylglycylhistidine and histidyltyrosine were oxidatively decomposed in the presence of copper ion to free peptide, N(alpha)-formyl peptide, and the sugar moieties of glucosone and arabinose. The formation of N(alpha)-formyl peptide was especially dependent on the concentrations of copper ion. Copper(II)-catalyzed autoxidative decomposition of Amadori compound to free peptide and glucosone has been clarified in our previous study, but the formation of N(alpha)-formyl peptide and arabinose was a novel pathway confirmed in this study. The results indicated the complexity of metal ion-catalyzed oxidation of Amadori derivatives in glycated protein, and this novel pathway may be useful for studying the amino-carbonyl reaction related with diabetic complications and aging.