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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 1H NMR spectrum of alditol 2 was identical to the product released by β-elimination from the parasite mucin. © The Royal Society of Chemistry 2012.

Registro:

Documento: Artículo
Título:Synthesis of the O-linked hexasaccharide containing β-d-Galf- (1→2)-β-d-Galf in Trypanosoma cruzi mucins
Autor:Kashiwagi, G.A.; Mendoza, V.M.; De Lederkremer, R.M.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Carbohydrates; Carboxylic acids; Cyanides; Esterification; Nuclear magnetic resonance spectroscopy; Diastereoselective; H NMR spectra; Hexasaccharides; Novel precursors; O-linked; Parasite-; Reducing ends; Sialic acids; Sialylation; Synthons; Trans-sialidases; Trypanosoma cruzi; Glycosylation; Trypanosoma cruzi
Año:2012
Volumen:10
Número:31
Página de inicio:6322
Página de fin:6332
DOI: http://dx.doi.org/10.1039/c2ob25741f
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v10_n31_p6322_Kashiwagi

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Citas:

---------- APA ----------
Kashiwagi, G.A., Mendoza, V.M., De Lederkremer, R.M. & Gallo-Rodriguez, C. (2012) . Synthesis of the O-linked hexasaccharide containing β-d-Galf- (1→2)-β-d-Galf in Trypanosoma cruzi mucins. Organic and Biomolecular Chemistry, 10(31), 6322-6332.
http://dx.doi.org/10.1039/c2ob25741f
---------- CHICAGO ----------
Kashiwagi, G.A., Mendoza, V.M., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of the O-linked hexasaccharide containing β-d-Galf- (1→2)-β-d-Galf in Trypanosoma cruzi mucins" . Organic and Biomolecular Chemistry 10, no. 31 (2012) : 6322-6332.
http://dx.doi.org/10.1039/c2ob25741f
---------- MLA ----------
Kashiwagi, G.A., Mendoza, V.M., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of the O-linked hexasaccharide containing β-d-Galf- (1→2)-β-d-Galf in Trypanosoma cruzi mucins" . Organic and Biomolecular Chemistry, vol. 10, no. 31, 2012, pp. 6322-6332.
http://dx.doi.org/10.1039/c2ob25741f
---------- VANCOUVER ----------
Kashiwagi, G.A., Mendoza, V.M., De Lederkremer, R.M., Gallo-Rodriguez, C. Synthesis of the O-linked hexasaccharide containing β-d-Galf- (1→2)-β-d-Galf in Trypanosoma cruzi mucins. Org. Biomol. Chem. 2012;10(31):6322-6332.
http://dx.doi.org/10.1039/c2ob25741f