Specific Degradation of an N-acetylglucosamine-Containing Polysaccharide (hyaluronic acid) by Hydrogen Peroxide Under the Mediation of cupric ion

To explore new biopolymer-degrading methods that are simple, specific, and effective, a cupric ion and hydrogen peroxide system was investigated for its ability to oxidatively fragment N-acetylglucosamine-containing polysaccharides, exemplified by hyaluronic acid. Treating hyaluronic acid with cupric ion and hydrogen peroxide led to depolymerization, whose extent depended on the concentrations of cupric ion and peroxide. Fragmented hyaluronic acids with defined size were obtained, indicating an apparent region-specificity of the reaction. The effect was attributed to a specific cupric ion binding to the N-acetylglucosamines, a cupric ion activation of hydrogen peroxide to form reactive oxygen species, and restricted oxidative cleavage of the glycosidic bonds. Such region-specificity might render the simple chemical depolymerization method useful for targeted biodegradation applications.