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...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v343_n10-11_p1870_GandolfiDonadio |
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todo:paper_00086215_v343_n10-11_p1870_GandolfiDonadio2023-10-03T14:07:17Z Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan Gandolfi-Donadío, L. Gallo-Rodriguez, C. de Lederkremer, R.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, L. Gallo-Rodriguez, C. de Lederkremer, R.M. 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. |
| format |
JOUR |
| author |
Gandolfi-Donadío, L. Gallo-Rodriguez, C. de Lederkremer, R.M. |
| author_facet |
Gandolfi-Donadío, L. Gallo-Rodriguez, C. de Lederkremer, R.M. |
| author_sort |
Gandolfi-Donadío, L. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v343_n10-11_p1870_GandolfiDonadio |
| work_keys_str_mv |
AT gandolfidonadiol synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan AT gallorodriguezc synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan AT delederkremerrm synthesisofatetrasaccharidefragmentofmycobacterialarabinogalactan |
| _version_ |
1782025441774665728 |