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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todo:paper_00086215_v345_n3_p385_Mendoza2023-10-03T14:07:21Z Synthesis of trisaccharides containing internal galactofuranose O-linked in Trypanosoma cruzi mucins Mendoza, V.M. Kashiwagi, G.A. de Lederkremer, R.M. Gallo-Rodriguez, C. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 |
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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, V.M. Kashiwagi, G.A. de Lederkremer, R.M. Gallo-Rodriguez, C. 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. |
| format |
JOUR |
| author |
Mendoza, V.M. Kashiwagi, G.A. de Lederkremer, R.M. Gallo-Rodriguez, C. |
| author_facet |
Mendoza, V.M. Kashiwagi, G.A. de Lederkremer, R.M. Gallo-Rodriguez, C. |
| author_sort |
Mendoza, V.M. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v345_n3_p385_Mendoza |
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