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Synthesis of the O-linked hexasaccharide containing β-D-Galf-(1→2)-β-D-Galf in Trypanosoma cruzi mucins.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2012 Aug 21; Vol. 10 (31), pp. 6322-32. Date of Electronic Publication: 2012 Jun 26. - Publication Year :
- 2012
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Abstract
- The hexasaccharide β-D-Galp-(1→2)-[β-D-Galp-(1→3)]-β-D-Galp-(1→6)-[β-D-Galf(1→2)-β-D-Galf(1→4)]-D-GlcNAc (1) is the largest carbohydrate structure released as alditol by reductive β-elimination from mucins of some strains of T. cruzi. The terminal β-D-Galp units are sites of sialylation by trans-sialidase which transfers sialic acid from the host to the parasite. Hexasaccharide 1 was synthesized by a [3 + 3]-convergent strategy based on a nitrile assisted glycosylation, using the trichloroacetimidate method. The β-D-Galf-(1→2)-β-D-Galf-D-GlcNAc synthon was sequentially constructed from the reducing end to the non-reducing end employing benzyl α-D-galactofuranoside as starting material for the internal Galf unit. The choice of this novel precursor, obtained in one-reaction step from galactose, allowed the introduction of an orthogonal and participating levulinoyl group at O-2. Thus, the diastereoselective construction of the Galf-β(1→4)-GlcNAc linkage by the trichloroacetimidate method of glycosylation was achieved. The (1)H NMR spectrum of alditol 2 was identical to the product released by β-elimination from the parasite mucin.
- Subjects :
- Carbohydrate Sequence
Galactose chemical synthesis
Galactose chemistry
Glycosylation
Molecular Sequence Data
Oligosaccharides chemistry
Sugar Alcohols chemical synthesis
Sugar Alcohols chemistry
Mucins chemistry
Oligosaccharides chemical synthesis
Protozoan Proteins chemistry
Trypanosoma cruzi chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 10
- Issue :
- 31
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 22735493
- Full Text :
- https://doi.org/10.1039/c2ob25741f