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Quetard, C ; Bourgerie, S ; Normand-Sdiqui, N ; Mayer, R ; Strecker, G ; Midoux, P ; Roche, AC ; Monsigny, M

Novel glycosynthons for glycoconjugate preparation : Oligosaccharylpyroglutamylanilide derivatives

Bioconjugate Chemistry 9 (2) 268-276

par Administrateur - publié le

Abstract :

The reducing sugar of an oligosaccharide reacting with the a-amino group of an amino acid is converted to an N-oligosaccharylamino acid which can then be stabilized by N-acylation. Oligosaccharides in solution in N,N-dimethylformamide reacted with a-glutamyl-p-nitroanilide at 50 degrees C for a few hours, leading to an N-oligosaccharylglutamyl-p-nitroanilide. Then, the gamma-carboxylic group of the glutamyl moiety, activated by adding (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), reacted with the substituted a-amino group of the glutamyl residue, leading to an N-oligosaccharylpyroglutamyl-p-nitroanilide within 0.5 h.