Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi

The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-G...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Gallo, Carola, Mendoza, Verónica María, Muchnik de Lederkremer, Rosa María
Publicado:	2002
Materias:	D-galactono-1,4-lactone Galactofuranose Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine mucin polysaccharide unclassified drug article conformation elimination reaction isomerism nonhuman polymerization priority journal reduction synthesis Trypanosoma
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v58_n46_p9373_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_00404020_v58_n46_p9373_GalloRodriguez
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404020_v58_n46_p9373_GalloRodriguez
record_format	dspace
spelling	paper:paper_00404020_v58_n46_p9373_GalloRodriguez2023-06-08T15:04:15Z Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi Gallo, Carola Mendoza, Verónica María Muchnik de Lederkremer, Rosa María D-galactono-1,4-lactone Galactofuranose Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine mucin polysaccharide unclassified drug article conformation elimination reaction isomerism nonhuman polymerization priority journal reduction synthesis Trypanosoma cruzi Trypanosoma Trypanosoma cruzi The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-Galf-(1→4)-D-GlcNAc with a donor derivative of β-D-Galp-(1→3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the β-D-Galp-(1→3)-D-Galf unit is described. © 2002 Elsevier Science Ltd. All rights reserved. Fil:Gallo-Rodriguez, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 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. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v58_n46_p9373_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_00404020_v58_n46_p9373_GalloRodriguez
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	D-galactono-1,4-lactone Galactofuranose Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine mucin polysaccharide unclassified drug article conformation elimination reaction isomerism nonhuman polymerization priority journal reduction synthesis Trypanosoma cruzi Trypanosoma Trypanosoma cruzi
spellingShingle	D-galactono-1,4-lactone Galactofuranose Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine mucin polysaccharide unclassified drug article conformation elimination reaction isomerism nonhuman polymerization priority journal reduction synthesis Trypanosoma cruzi Trypanosoma Trypanosoma cruzi Gallo, Carola Mendoza, Verónica María Muchnik de Lederkremer, Rosa María Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
topic_facet	D-galactono-1,4-lactone Galactofuranose Glycosylation Mucins Trichloroacetimidate Trypanosoma cruzi beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine mucin polysaccharide unclassified drug article conformation elimination reaction isomerism nonhuman polymerization priority journal reduction synthesis Trypanosoma cruzi Trypanosoma Trypanosoma cruzi
description	The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-Galf-(1→4)-D-GlcNAc with a donor derivative of β-D-Galp-(1→3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the β-D-Galp-(1→3)-D-Galf unit is described. © 2002 Elsevier Science Ltd. All rights reserved.
author	Gallo, Carola Mendoza, Verónica María Muchnik de Lederkremer, Rosa María
author_facet	Gallo, Carola Mendoza, Verónica María Muchnik de Lederkremer, Rosa María
author_sort	Gallo, Carola
title	Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
title_short	Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
title_full	Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
title_fullStr	Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
title_full_unstemmed	Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
title_sort	synthesis of β-d-galp-(1→3)-β-d-galp-(1→6)-[β-d-galf- (1→4)]-d-glcnac, a tetrasaccharide component of mucins of trypanosoma cruzi
publishDate	2002
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v58_n46_p9373_GalloRodriguez http://hdl.handle.net/20.500.12110/paper_00404020_v58_n46_p9373_GalloRodriguez
work_keys_str_mv	AT gallocarola synthesisofbdgalp13bdgalp16bdgalf14dglcnacatetrasaccharidecomponentofmucinsoftrypanosomacruzi AT mendozaveronicamaria synthesisofbdgalp13bdgalp16bdgalf14dglcnacatetrasaccharidecomponentofmucinsoftrypanosomacruzi AT muchnikdelederkremerrosamaria synthesisofbdgalp13bdgalp16bdgalf14dglcnacatetrasaccharidecomponentofmucinsoftrypanosomacruzi
_version_	1768546011936980992

Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi

Ejemplares similares