Mechanism of acid hydrolysis of N-acetyl-D-glucosamine

The hydrolysis kinetics of the chitin monomer, N-acetyl-D-glucosamine, in HCl, HClO4, and H3PO4 was studied in relation to the acid concentration. The rate constants of N-acetyl-D-glucosamine deacetylation and D(+)-glucosamine formation in HClO4 and H3PO4 were determined for the first time. The rate of the acetamide bond hydrolysis in N-acetyl-D-glucosamine depends on the concentrations of hydrogen ions and water. The nucleophilicity of the acid residues does not affect the rate of N-acetyl-D-glucosamine hydrolysis.