Hydrazinolysis-N-reacetylation of glycopeptides and glycoproteins. Model studies using 2-acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosy lamine.
2-Acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosyla mine (1) was used as a model glycopeptide to study the hydrazinolysis-N-reacetylation procedure. The major, initial product was the beta-acetohydrazide derivative of 2-acetamido-2-deoxy-D-glucose (2) which gave 2-acetamido-2-deoxy-D-glucose (5) after exposure to acidic conditions. Very mild conditions of hydrolysis of 2 gave a 75-80% overall yield of 5 from 1 after the hydrazinolysis-N-reacetylation procedure. Several other minor compounds were detected which were not converted into 5 upon mild acid hydrolysis, indicating that 20-25% of product cannot be recovered as 5 at the reducing end of oligosaccharides.
D000107:Acetylation; D000117:Acetylglucosamine / Q000031:analogs & derivatives*; D055598:Chemical Phenomena; D002621:Chemistry; D005944:Glucosamine / Q000031:analogs & derivatives*; D006020:Glycopeptides; D006023:Glycoproteins; D006834:Hydrazines; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D006020:Glycopeptides; D006023:Glycoproteins; D006834:Hydrazines; D007202:Indicators and Reagents; C000009:N-acetylglucosaminylasparagine; C029424:hydrazine; D005944:Glucosamine; D000117:Acetylglucosamine