Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan

The arabinogalactan of mycobacteria contains both monosaccharides in the furanose ring form, which are absent in mammals. We report here the first synthesis of the tetrasaccharide fragment α-d-Araf-(1→5)-β-d-Galf-(1→5)-β-d-Galf-(1→6)-d-Galf, conveniently derivatized for further elongation. The strat...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Gandolfi Donadío, Lucía, Gallo, Carola, Muchnik de Lederkremer, Rosa María
Publicado:	2008
Materias:	Arabinofuranose Arabinogalactan Galactofuranose Galactonolactone Mycobacteria Biosynthesis Mammals Monosaccharides Mycobacterial arabinogalactan Tetrasaccharide fragment Bacteria arabinogalactan galactofuranose galactose lactone derivative tetrasaccharide article carbohydrate synthesis Mycobacterium priority journal Carbohydrate Sequence Galactans Mycobacterium tuberculosis Oligosaccharides Corynebacterineae Mammalia
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n10-11_p1870_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00086215_v343_n10-11_p1870_GandolfiDonadio
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00086215_v343_n10-11_p1870_GandolfiDonadio
record_format	dspace
spelling	paper:paper_00086215_v343_n10-11_p1870_GandolfiDonadio2023-06-08T14:32:54Z Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Arabinofuranose Arabinogalactan Galactofuranose Galactonolactone Mycobacteria Biosynthesis Mammals Monosaccharides Mycobacterial arabinogalactan Tetrasaccharide fragment Bacteria arabinogalactan galactofuranose galactose lactone derivative tetrasaccharide article carbohydrate synthesis Mycobacterium priority journal Carbohydrate Sequence Galactans Mycobacterium tuberculosis Oligosaccharides Corynebacterineae Mammalia The arabinogalactan of mycobacteria contains both monosaccharides in the furanose ring form, which are absent in mammals. We report here the first synthesis of the tetrasaccharide fragment α-d-Araf-(1→5)-β-d-Galf-(1→5)-β-d-Galf-(1→6)-d-Galf, conveniently derivatized for further elongation. The strategy relied on the use of suitably substituted d-galactono-1,4-lactones as precursors for the galactofuranose units. Reduction of lactone tetrasaccharide 9 with disiamylborane afforded the tetrasaccharide synthon 1. The tetrasaccharide contains the linker unit of the arabinan to the galactan. © 2008 Elsevier Ltd. All rights reserved. Fil:Gandolfi-Donadío, 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. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n10-11_p1870_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00086215_v343_n10-11_p1870_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	Arabinofuranose Arabinogalactan Galactofuranose Galactonolactone Mycobacteria Biosynthesis Mammals Monosaccharides Mycobacterial arabinogalactan Tetrasaccharide fragment Bacteria arabinogalactan galactofuranose galactose lactone derivative tetrasaccharide article carbohydrate synthesis Mycobacterium priority journal Carbohydrate Sequence Galactans Mycobacterium tuberculosis Oligosaccharides Corynebacterineae Mammalia
spellingShingle	Arabinofuranose Arabinogalactan Galactofuranose Galactonolactone Mycobacteria Biosynthesis Mammals Monosaccharides Mycobacterial arabinogalactan Tetrasaccharide fragment Bacteria arabinogalactan galactofuranose galactose lactone derivative tetrasaccharide article carbohydrate synthesis Mycobacterium priority journal Carbohydrate Sequence Galactans Mycobacterium tuberculosis Oligosaccharides Corynebacterineae Mammalia Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
topic_facet	Arabinofuranose Arabinogalactan Galactofuranose Galactonolactone Mycobacteria Biosynthesis Mammals Monosaccharides Mycobacterial arabinogalactan Tetrasaccharide fragment Bacteria arabinogalactan galactofuranose galactose lactone derivative tetrasaccharide article carbohydrate synthesis Mycobacterium priority journal Carbohydrate Sequence Galactans Mycobacterium tuberculosis Oligosaccharides Corynebacterineae Mammalia
description	The arabinogalactan of mycobacteria contains both monosaccharides in the furanose ring form, which are absent in mammals. We report here the first synthesis of the tetrasaccharide fragment α-d-Araf-(1→5)-β-d-Galf-(1→5)-β-d-Galf-(1→6)-d-Galf, conveniently derivatized for further elongation. The strategy relied on the use of suitably substituted d-galactono-1,4-lactones as precursors for the galactofuranose units. Reduction of lactone tetrasaccharide 9 with disiamylborane afforded the tetrasaccharide synthon 1. The tetrasaccharide contains the linker unit of the arabinan to the galactan. © 2008 Elsevier Ltd. All rights reserved.
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 a tetrasaccharide fragment of mycobacterial arabinogalactan
title_short	Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
title_full	Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
title_fullStr	Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
title_full_unstemmed	Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
title_sort	synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan
publishDate	2008
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n10-11_p1870_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00086215_v343_n10-11_p1870_GandolfiDonadio
work_keys_str_mv	AT gandolfidonadiolucia synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan AT gallocarola synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan AT muchnikdelederkremerrosamaria synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan
_version_	1768546610312118272

Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan

Ejemplares similares