Chromatographic separation of Lewis a and Lewis x oligosaccharides as glycosynthons
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- 作者：Frison ; Natacha ; Meunier ; Laurent ; Marceau ; Philippe ; Qué ; tard ; Christophe ; Strecker ; Gé ; rard ; et. al.
- 关键词：Glycosynthons ; Anion-exchange HPLC ; Hydrazinolysis ; Lewis a ; Lewis x ; NMR ; N-oligosaccharyl-pyroglutamyl derivatives ; β ; Ala ; β ; -Alanine ; BOP ; (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluoro-phosphate ; HPAEC ; high performance anion-
- 刊名：Biochimie
- 出版年：2003
- 出版时间：January - February, 2003
- 年：2003
- 卷：85
- 期：1-2
- 页码：47-51
- 全文大小：195 K
文摘
Lewis a and Lewis x oligosaccharides Galβ3(Fucα4)GlcNAcβ3Galβ4Glc and Galβ4(Fucα3)GlcNAcβ3Galβ4Glc 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 [Galβ3(Fucα4)GlcNAcβ3Galβ4Glc-Glp-βAla-OBzl and Galβ4(Fucα3)GlcNAcβ3Galβ4Glc-Glp-βAla-OBzl] after substitution of the terminal reducing sugar by a short peptide (pyroglutamyl-βalanyl-O-benzyl ester) in a one-pot two-step reaction (Carbohydr. Lett. 1 (1995) 269; Bioconjug. Chem. 9 (1998) 268). Such glycosynthons are easily either converted back to native Lewis a and Lewis x oligosaccharides upon hydrazinolysis or used to synthesize glycoconjugates, such as glycoclusters, glycopeptides, glycooligonucleotides, glycosylated polymers or glycosylated matrices for therapeutic or analytical purposes.