MODEL STUDIES PERTAINING TO THE HYDRAZINOLYSIS OF GLYCOPEPTIDES AND GLYCOPROTEINS: HYDRAZINOLYSIS OF THE 1-N-ACETYL AND 1-N-(L-β-ASPARTYL) DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYLAMINE

Article abstract of DOI:10.1016/S0008-6215(00)85432-4

The products of hydrazinolysis of the 1-N-acetyl and 1-N-(L-β-aspartyl) derivatives of 2-acetamido-2-deoxy-β-D-glucopyranosylamine could not be converted quantitatively into 2-amino-2-deoxy-D-glucose under mild conditions.Proton and (13)C-n.m.r. measurements indicated that the hydrazone of 2-amino-2-deoxy-D-glucose was a major product of the hydrazinolysis of 2-acetamido-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine.Control experiments showed that acetohydrazide is slowly converted into 4-amino-3,5-dimethyl-1,2,4-triazole under the conditions of hydrazinolysis, and hat 2-amino-2-deoxy-D-glucose reacts slowly with acetohydrazide in dilute acetic acid.The implications of these results in relation to the hydrazinolysis of glycopeptides and glycoproteins are discussed.