Chromatographic separation of Lewis a and Lewis x oligosaccharides as glycosynthons.
Lewis a and Lewis x oligosaccharides Gal beta 3(Fuc alpha 4)GlcNAc beta 3Gal beta 4Glc and Gal beta 4(Fuc alpha 3)GlcNAc beta 3Gal beta 4Glc 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 [Gal beta 3(Fuc alpha 4)GlcNAc beta 3Gal beta 4Glc-Glp-beta Ala-OBzl and Gal beta 4(Fuc alpha 3)GlcNAc beta 3Gal beta 4Glc-Glp-beta Ala-OBzl] after substitution of the terminal reducing sugar by a short peptide (pyroglutamyl-beta alanyl-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.
Frison
Natacha
N
Vectorisation et Trafic Intracellulaire, Glycobiologie, Centre de Biophysique Moléculaire, Centre National de la Recherche scientifique, rue Charles-Sadron, 45071 Orleans cedex 2, France.
Meunier
Laurent
L
Marceau
Philippe
P
Quétard
Christophe
C
Strecker
Gérard
G
Roche
Annie-Claude
AC
Mayer
Roger
R
Monsigny
Michel
M
D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002852:Chromatography, Ion Exchange; D006020:Glycopeptides / Q000138:chemical synthesis / Q000302:isolation & purification; D006031:Glycosylation; D006801:Humans; D006834:Hydrazines; D007983:Lewis Blood Group Antigens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization
D006020:Glycopeptides; D006834:Hydrazines; D007983:Lewis Blood Group Antigens; C494219:Lewis a oligosaccharide; D009844:Oligosaccharides; C029424:hydrazine