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Abstract:

The trisaccharides β-d-Galf-(1→2)-β-d-Galf-(1→4)-d-GlcNAc (5) and β-d-Galp-(1→2)-β-d-Galf-(1→4)-d-GlcNAc (6) constitute novel structures isolated as alditols when released by reductive β-elimination from mucins of Trypanosoma cruzi (Tulahuen strain). Trisaccharides 5 and 6 were synthesized employing the aldonolactone approach. Thus, a convenient d-galactono-1,4-lactone derivative was used for the introduction of the internal galactofuranose and the trichloroacetimidate method was employed for glycosylation reactions. Due to the lack of anchimeric assistance on O-2 of the galactofuranosyl precursor, glycosylation studies were performed under different conditions. The nature of the solvent strongly determined the stereochemical course of the glycosylation reactions when the galactofuranosyl donor was substituted either by 2-O-Galp or 2-O-Galf. © 2009 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
Autor:Mendoza, V.M.; Kashiwagi, G.A.; de Lederkremer, R.M.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Palabras clave:Galactofuranose; Galactonolactone; Mucin; Trichloroacetimidate glycosylation; Trisaccharide; Trypanosoma cruzi; Alditols; Galactofuranose; Glycosylation reactions; Novel structures; O-linked; Trypanosoma cruzi; Glycosylation; Synthesis (chemical); Esterification; galactofuranose; galactofuranosyl; galactonolactone; mucin; oligosaccharide; solvent; trichloroacetimidic acid; trisaccharide; unclassified drug; article; biosynthesis; carbohydrate synthesis; glycosylation; nonhuman; priority journal; stereochemistry; Trypanosoma cruzi; Carbohydrate Sequence; Mucins; Nuclear Magnetic Resonance, Biomolecular; Stereoisomerism; Trisaccharides; Trypanosoma cruzi; Trypanosoma cruzi
Año:2010
Volumen:345
Número:3
Página de inicio:385
Página de fin:396
DOI: http://dx.doi.org/10.1016/j.carres.2009.12.005
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Mucins; Trisaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v345_n3_p385_Mendoza

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Citas:

---------- APA ----------
Mendoza, V.M., Kashiwagi, G.A., de Lederkremer, R.M. & Gallo-Rodriguez, C. (2010) . Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins. Carbohydrate Research, 345(3), 385-396.
http://dx.doi.org/10.1016/j.carres.2009.12.005
---------- CHICAGO ----------
Mendoza, V.M., Kashiwagi, G.A., de Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins" . Carbohydrate Research 345, no. 3 (2010) : 385-396.
http://dx.doi.org/10.1016/j.carres.2009.12.005
---------- MLA ----------
Mendoza, V.M., Kashiwagi, G.A., de Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins" . Carbohydrate Research, vol. 345, no. 3, 2010, pp. 385-396.
http://dx.doi.org/10.1016/j.carres.2009.12.005
---------- VANCOUVER ----------
Mendoza, V.M., Kashiwagi, G.A., de Lederkremer, R.M., Gallo-Rodriguez, C. Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins. Carbohydr. Res. 2010;345(3):385-396.
http://dx.doi.org/10.1016/j.carres.2009.12.005