Behaviour of dehydroalanine derivatives under hydrazinolysis conditions. Possible relevance to glycoprotein hydrazinolysis.
Reactions that are relevant to the cleavage, by hydrazinolysis, of O-linked oligosaccharides from glycoproteins were studied using dehydroalanine derivatives as models of the intermediates formed from O-glycosylated serine residues. Conjugate addition of hydrazine followed by cyclisation to form pyrazolidinones, if occurring during glycoprotein hydrazinolysis, could reduce the yield of released oligosaccharide. However, N-acetyldehydroalanine amide derivatives, which modelled the dehydroalanine derivatives believed to be intermediates in the hydrazinolysis of glycoproteins containing O-linked oligosaccharides, underwent conjugate addition but no cyclisation.
Suzen
S
S
Chemistry Department, University of Wales Swansea, Swansea, UK.
Williams
M
M
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D002625:Chemistry, Organic; D006023:Glycoproteins / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D055601:Organic Chemistry Phenomena
D006023:Glycoproteins; D006834:Hydrazines; C015102:dehydroalanine; D000409:Alanine