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Abstract:

The arabinogalactan is a crucial constituent of the cell wall of mycobacteria. Both monosaccharides (arabinose and galactose) are found in the furanose configuration, absent in mammals. An efficient synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan, is described. The strategy relies on the use of a conveniently substituted D-galactono-1,4-lactone as a precursor of the reducing furanose ring. The glycosylation step was performed by the tin(IV) chloride promoted method using 1,2,3,5-tetra-O-benzoyl-α,β-D-arabinofuranose. The arabinose donor was obtained in a crystalline state in one step by benzoylation of arabinose in hot pyridine. Selective glycosylation of the exocyclic OH-5 was obtained in 75% yield to give 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl- (1→5)-2,6-di-O-pivaloyl-D-galactono-1,4-lactone. Reduction with disiamylborane gave the disaccharide synthon, useful for further glycosylations. Dec-9-enyl α-D-Araf-(1→5)-β-D-Galf, a convenient substrate for arabinofuranosyl transferases studies, was obtained by the trichloroacetimidate method of glycosylation. © 2006 NRC Canada.

Registro:

Documento: Artículo
Título:Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis
Autor:Gandolfi-Donadío, L.; Gallo-Rodriguez, C.; De Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Arabinofuranose; Galactofuranose; Mycobacterium arabinogalactan; Tin(IV) chloride; Trichloroacetimidate; Biomedical engineering; Crystalline materials; Reduction; Substrates; Synthesis (chemical); Tin compounds; Arabinofuranose; Galactofuranose; Glycosylation; Mycobacterium arabinogalactan; Tin(IV) chloride; Trichloroacetimidate; Bacteria; 1,2,3,5 tetra o benzoyl alpha beta dextro arabinofuranose; 2,3,5 tri o benzoyl alpha dextro arabinofuranosyl(1-5) 2,6 di o pivaloyl dextro galactono 1,4 lactone; arabinogalactan; borane derivative; dextro galactono 1,4 lactone; disaccharide; disiamylborane; furan derivative; galactan; hydroxyl group; lactone derivative; pyridine; tin chloride; transferase; unclassified drug; article; crystallization; glycosylation; Mycobacterium tuberculosis; synthesis
Año:2006
Volumen:84
Número:4
Página de inicio:486
Página de fin:491
DOI: http://dx.doi.org/10.1139/V06-025
Título revista:Canadian Journal of Chemistry
Título revista abreviado:Can. J. Chem.
ISSN:00084042
CODEN:CJCHA
CAS:arabinogalactan, 9036-66-2; galactan, 39300-87-3, 9037-55-2; pyridine, 110-86-1; tin chloride, 1344-13-4; transferase, 9047-61-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00084042_v84_n4_p486_GandolfiDonadio

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Citas:

---------- APA ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C. & De Lederkremer, R.M. (2006) . Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis. Canadian Journal of Chemistry, 84(4), 486-491.
http://dx.doi.org/10.1139/V06-025
---------- CHICAGO ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., De Lederkremer, R.M. "Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis" . Canadian Journal of Chemistry 84, no. 4 (2006) : 486-491.
http://dx.doi.org/10.1139/V06-025
---------- MLA ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., De Lederkremer, R.M. "Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis" . Canadian Journal of Chemistry, vol. 84, no. 4, 2006, pp. 486-491.
http://dx.doi.org/10.1139/V06-025
---------- VANCOUVER ----------
Gandolfi-Donadío, L., Gallo-Rodriguez, C., De Lederkremer, R.M. Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis. Can. J. Chem. 2006;84(4):486-491.
http://dx.doi.org/10.1139/V06-025