Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids

The synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introducti...

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Autores principales:	Gandolfi Donadío, Lucía, Gallo, Carola, Muchnik de Lederkremer, Rosa María
Publicado:	2002
Materias:	Glycosidation Reduction Polysaccharides alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose beta dextro galactofuranosyl (1-3) dextro mannose borane derivative diisoamylborane disaccharide lactone lipophosphoglycan phosphatidylinositide trichloroacetimidic acid trisaccharide unclassified drug article carbohydrate synthesis chemical reaction glycosylation Leishmania reduction Trypanosoma cruzi Animals Carbohydrate Sequence Catalysis Chemistry, Organic Chromatography, Thin Layer Glycosphingolipids Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure Trisaccharides
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v67_n13_p4430_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v67_n13_p4430_GandolfiDonadio
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00223263_v67_n13_p4430_GandolfiDonadio
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spelling	paper:paper_00223263_v67_n13_p4430_GandolfiDonadio2023-06-08T14:49:33Z Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Glycosidation Reduction Polysaccharides alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose beta dextro galactofuranosyl (1-3) dextro mannose borane derivative diisoamylborane disaccharide lactone lipophosphoglycan phosphatidylinositide trichloroacetimidic acid trisaccharide unclassified drug article carbohydrate synthesis chemical reaction glycosylation Leishmania reduction Trypanosoma cruzi Animals Carbohydrate Sequence Catalysis Chemistry, Organic Chromatography, Thin Layer Glycosphingolipids Leishmania Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure Trisaccharides Trypanosoma cruzi The synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the β-D-Galf-(1-3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported. Fil:Gandolfi-Donadio, L. 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. 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_00223263_v67_n13_p4430_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v67_n13_p4430_GandolfiDonadio
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Glycosidation Reduction Polysaccharides alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose beta dextro galactofuranosyl (1-3) dextro mannose borane derivative diisoamylborane disaccharide lactone lipophosphoglycan phosphatidylinositide trichloroacetimidic acid trisaccharide unclassified drug article carbohydrate synthesis chemical reaction glycosylation Leishmania reduction Trypanosoma cruzi Animals Carbohydrate Sequence Catalysis Chemistry, Organic Chromatography, Thin Layer Glycosphingolipids Leishmania Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure Trisaccharides Trypanosoma cruzi
spellingShingle	Glycosidation Reduction Polysaccharides alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose beta dextro galactofuranosyl (1-3) dextro mannose borane derivative diisoamylborane disaccharide lactone lipophosphoglycan phosphatidylinositide trichloroacetimidic acid trisaccharide unclassified drug article carbohydrate synthesis chemical reaction glycosylation Leishmania reduction Trypanosoma cruzi Animals Carbohydrate Sequence Catalysis Chemistry, Organic Chromatography, Thin Layer Glycosphingolipids Leishmania Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure Trisaccharides Trypanosoma cruzi Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
topic_facet	Glycosidation Reduction Polysaccharides alpha dextro galactopyranosyl (1-3) beta dextro galactofuranosyl (1-3) dextro mannose beta dextro galactofuranosyl (1-3) dextro mannose borane derivative diisoamylborane disaccharide lactone lipophosphoglycan phosphatidylinositide trichloroacetimidic acid trisaccharide unclassified drug article carbohydrate synthesis chemical reaction glycosylation Leishmania reduction Trypanosoma cruzi Animals Carbohydrate Sequence Catalysis Chemistry, Organic Chromatography, Thin Layer Glycosphingolipids Leishmania Magnetic Resonance Spectroscopy Molecular Sequence Data Molecular Structure Trisaccharides Trypanosoma cruzi
description	The synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, present in the type-2 glycoinositolphospholipids and in the core of the lipophosphoglycan of Leishmania, is described. The glycosyl aldonolactone approach, followed by reduction of the lactone with diisoamylborane, was utilized for the introduction of the internal galactofuranosyl unit and the trichloroacetimidate method for the O-glycosidation reaction. A high-yield synthesis of the β-D-Galf-(1-3)-D-Man unit, also present in the lipopeptidophosphoglycan of Trypanosoma cruzi, is reported.
author	Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María
author_facet	Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María
author_sort	Gandolfi Donadío, Lucía
title	Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
title_short	Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
title_full	Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
title_fullStr	Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
title_full_unstemmed	Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
title_sort	synthesis of α-d-galp-(1→3)-β-d-galf-(1→3)-d-man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids
publishDate	2002
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v67_n13_p4430_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v67_n13_p4430_GandolfiDonadio
work_keys_str_mv	AT gandolfidonadiolucia synthesisofadgalp13bdgalf13dmanaterminaltrisaccharideofleishmaniatype2glycoinositolphospholipids AT gallocarola synthesisofadgalp13bdgalf13dmanaterminaltrisaccharideofleishmaniatype2glycoinositolphospholipids AT muchnikdelederkremerrosamaria synthesisofadgalp13bdgalf13dmanaterminaltrisaccharideofleishmaniatype2glycoinositolphospholipids
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Synthesis of α-D-Galp-(1→3)-β-D-Galf-(1→3)-D-Man, a terminal trisaccharide of leishmania type-2 glycoinositolphospholipids

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