Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan |
Autor: | Gandolfi-Donadío, L.; Gallo-Rodriguez, C.; de Lederkremer, R.M. |
Filiación: | CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
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Palabras clave: | 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 |
Año: | 2008
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Volumen: | 343
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Número: | 10-11
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Página de inicio: | 1870
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Página de fin: | 1875
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DOI: |
http://dx.doi.org/10.1016/j.carres.2008.01.024 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | Carbohydr. Res.
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ISSN: | 00086215
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CODEN: | CRBRA
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CAS: | arabinogalactan, 9036-66-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; arabinogalactan, 9036-66-2; Galactans; Oligosaccharides
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n10-11_p1870_GandolfiDonadio |
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Citas:
---------- APA ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C. & de Lederkremer, R.M.
(2008)
. Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan. Carbohydrate Research, 343(10-11), 1870-1875.
http://dx.doi.org/10.1016/j.carres.2008.01.024---------- CHICAGO ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., de Lederkremer, R.M.
"Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan"
. Carbohydrate Research 343, no. 10-11
(2008) : 1870-1875.
http://dx.doi.org/10.1016/j.carres.2008.01.024---------- MLA ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., de Lederkremer, R.M.
"Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan"
. Carbohydrate Research, vol. 343, no. 10-11, 2008, pp. 1870-1875.
http://dx.doi.org/10.1016/j.carres.2008.01.024---------- VANCOUVER ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., de Lederkremer, R.M. Synthesis of a tetrasaccharide fragment of mycobacterial arabinogalactan. Carbohydr. Res. 2008;343(10-11):1870-1875.
http://dx.doi.org/10.1016/j.carres.2008.01.024