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Frison, N ; Meunier, L ; Marceau, P ; Quetard, C ; Strecker, G ; Roche, AC ; Mayer, R ; Monsigny, M

Chromatographic separation of Lewis a and Lewis x oligosaccharides as glycosynthons

Biochimie 85 (1-2) 47-51

par Administrateur - publié le , mis à jour le

Abstract :

Lewis a and Lewis x oligosaccharides Galbeta3(Fucalpha4)GlcNAcbeta3Galbeta4Glc and Galbeta4(Fucalpha3)GlcNAcbeta3Galbeta4Glc are easily isolated as a mixture from biological fluids, including human milk. However, because they behave almost identically in most chromatographic systems, it is difficult to have each of them as a pure compound. Incidentally, we found that they were easily separated by HPLC as glycosynthons [Galbeta3(Fucalpha4)GlcNAcbeta3Galbeta4Glc-Glp-betaAla-OBzl and Galbeta4(Fucalpha3)GlcNAcbeta3Galbeta4Glc-Glp-betaAla-OBzl] after substitution of the terminal reducing sugar by a short peptide (pyroglutamyl-betaalanyl-O-benzyl ester) in a one-pot two-step reaction (Carbohydr. Lett. 1 (1995) 269 ; Bioconjug. Chem. 9 (1998) 268).