Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

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...

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Autores principales:	Mendoza, Verónica María, Muchnik de Lederkremer, Rosa María, Gallo, Carola
Publicado:	2010
Materias:	Galactofuranose Galactonolactone Mucin Trichloroacetimidate glycosylation Trisaccharide Trypanosoma cruzi Alditols Glycosylation reactions Novel structures O-linked Glycosylation Synthesis (chemical) Esterification galactofuranose galactofuranosyl galactonolactone mucin oligosaccharide solvent trichloroacetimidic acid trisaccharide unclassified drug article biosynthesis carbohydrate synthesis glycosylation nonhuman priority journal stereochemistry Carbohydrate Sequence Mucins Nuclear Magnetic Resonance, Biomolecular Stereoisomerism Trisaccharides
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v345_n3_p385_Mendoza http://hdl.handle.net/20.500.12110/paper_00086215_v345_n3_p385_Mendoza
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	paper:paper_00086215_v345_n3_p385_Mendoza2023-06-08T14:32:58Z Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola 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 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. Fil:Mendoza, V.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gallo-Rodriguez, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v345_n3_p385_Mendoza http://hdl.handle.net/20.500.12110/paper_00086215_v345_n3_p385_Mendoza
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
topic_facet	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
description	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.
author	Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola
author_facet	Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Gallo, Carola
author_sort	Mendoza, Verónica María
title	Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
title_short	Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
title_full	Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
title_fullStr	Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
title_full_unstemmed	Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins
title_sort	synthesis of trisaccharides containing internal galactofuranose o-linked in trypanosoma cruzi mucins
publishDate	2010
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v345_n3_p385_Mendoza http://hdl.handle.net/20.500.12110/paper_00086215_v345_n3_p385_Mendoza
work_keys_str_mv	AT mendozaveronicamaria synthesisoftrisaccharidescontaininginternalgalactofuranoseolinkedintrypanosomacruzimucins AT muchnikdelederkremerrosamaria synthesisoftrisaccharidescontaininginternalgalactofuranoseolinkedintrypanosomacruzimucins AT gallocarola synthesisoftrisaccharidescontaininginternalgalactofuranoseolinkedintrypanosomacruzimucins
_version_	1768546425049710592

Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins

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