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Abstract:

Mycolyl-arabinogalactan (mAG) complex is a major component of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis disease. Due to the essentiality of the cell wall for mycobacterium viability, knowledge of the biosynthesis of the arabinogalactan is crucial for the development of new therapeutic agents. In this context, we have synthesized two new branched arabinogalactafuranose tetrasaccharides, decenyl β-d-Galf-(1→5)- β-d-Galf-(1→6)[α-d-Araf(1→5)]-β-d-Galf (1) and decenyl β-d-Galf-(1→6)-[α-d-Araf-(1→5)]-β-d-Galf-(1→5)- β-d-Galf (2), as interesting tools for arabinofuranosyl transferase studies. The aldonolactone strategy for the introduction of the internal d-Galf was employed, allowing the construction of oligosaccharides from the non-reducing to the reducing end. Moreover, a one-pot procedure was developed for the synthesis of trisaccharide lactone 21, precursor of 2, which involved a glycosylation-deprotection-glycosylation sequence, through the use of TMSOTf as catalyst of the trichloroacetimidate method as well as promoter of TBDMS deprotection. © 2011 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
Autor:Gandolfi-Donadío, L.; Santos, M.; De Lederkremer, R.M.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Arabinogalactan; Causative agents; Cell walls; Deprotection; Mycobacterial; Mycobacterium tuberculosis; New therapeutic agent; One-pot procedures; Reducing ends; Tetrasaccharides; Biochemistry; Glycosylation; Esterification; antiinfective agent; arabinofuranose; arabinogalactan; arabinose; drug derivative; furan; furan derivative; galactan; galactose; article; chemical structure; chemistry; synthesis; Anti-Bacterial Agents; Arabinose; Furans; Galactans; Galactose; Molecular Structure; Mycobacterium; Mycobacterium tuberculosis
Año:2011
Volumen:9
Número:7
Página de inicio:2085
Página de fin:2097
DOI: http://dx.doi.org/10.1039/c0ob00989j
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CAS:arabinogalactan, 9036-66-2; arabinose, 147-81-9; furan, 110-00-9; galactan, 39300-87-3, 9037-55-2; galactose, 26566-61-0, 50855-33-9, 59-23-4; Anti-Bacterial Agents; Arabinose, 147-81-9; Furans; Galactans; Galactose, 26566-61-0; arabinofuranose; arabinogalactan, 9036-66-2; furan, 110-00-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v9_n7_p2085_GandolfiDonadio

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Citas:

---------- APA ----------
Gandolfi-Donadío, L., Santos, M., De Lederkremer, R.M. & Gallo-Rodriguez, C. (2011) . Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan. Organic and Biomolecular Chemistry, 9(7), 2085-2097.
http://dx.doi.org/10.1039/c0ob00989j
---------- CHICAGO ----------
Gandolfi-Donadío, L., Santos, M., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan" . Organic and Biomolecular Chemistry 9, no. 7 (2011) : 2085-2097.
http://dx.doi.org/10.1039/c0ob00989j
---------- MLA ----------
Gandolfi-Donadío, L., Santos, M., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan" . Organic and Biomolecular Chemistry, vol. 9, no. 7, 2011, pp. 2085-2097.
http://dx.doi.org/10.1039/c0ob00989j
---------- VANCOUVER ----------
Gandolfi-Donadío, L., Santos, M., De Lederkremer, R.M., Gallo-Rodriguez, C. Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan. Org. Biomol. Chem. 2011;9(7):2085-2097.
http://dx.doi.org/10.1039/c0ob00989j