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...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00404020_v58_n46_p9373_GalloRodriguez |
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todo:paper_00404020_v58_n46_p9373_GalloRodriguez2023-10-03T14:50:41Z 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-Rodriguez, C. Gil-Libarona, M.A. Mendoza, V.M. de Lederkremer, R.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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-Rodriguez, C. Gil-Libarona, M.A. Mendoza, V.M. de Lederkremer, R.M. 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. |
| format |
JOUR |
| author |
Gallo-Rodriguez, C. Gil-Libarona, M.A. Mendoza, V.M. de Lederkremer, R.M. |
| author_facet |
Gallo-Rodriguez, C. Gil-Libarona, M.A. Mendoza, V.M. de Lederkremer, R.M. |
| author_sort |
Gallo-Rodriguez, C. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00404020_v58_n46_p9373_GalloRodriguez |
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