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Chromatographic separation of Lewis a and Lewis x oligosaccharides as glycosynthons.
- Source :
-
Biochimie [Biochimie] 2003 Jan-Feb; Vol. 85 (1-2), pp. 47-51. - Publication Year :
- 2003
-
Abstract
- 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.
- Subjects :
- Carbohydrate Sequence
Chromatography, Ion Exchange
Glycopeptides chemical synthesis
Glycopeptides isolation & purification
Glycosylation
Humans
Hydrazines
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Oligosaccharides isolation & purification
Spectrometry, Mass, Electrospray Ionization
Chromatography, High Pressure Liquid methods
Lewis Blood Group Antigens chemistry
Oligosaccharides chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 0300-9084
- Volume :
- 85
- Issue :
- 1-2
- Database :
- MEDLINE
- Journal :
- Biochimie
- Publication Type :
- Academic Journal
- Accession number :
- 12765774
- Full Text :
- https://doi.org/10.1016/s0300-9084(03)00073-7