Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan

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 develo...

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Autores principales: Gandolfi Donadío, Lucía, Muchnik de Lederkremer, Rosa María, Gallo, Carola
Publicado: 2011
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Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v9_n7_p2085_GandolfiDonadio
http://hdl.handle.net/20.500.12110/paper_14770520_v9_n7_p2085_GandolfiDonadio
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spelling paper:paper_14770520_v9_n7_p2085_GandolfiDonadio2023-06-08T16:18:07Z Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan Gandolfi Donadío, Lucía Muchnik de Lederkremer, Rosa María Gallo, Carola 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 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. Fil:Gandolfi-Donadío, L. 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. Fil:Gallo-Rodriguez, C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v9_n7_p2085_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_14770520_v9_n7_p2085_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 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
spellingShingle 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
Gandolfi Donadío, Lucía
Muchnik de Lederkremer, Rosa María
Gallo, Carola
Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
topic_facet 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
description 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.
author Gandolfi Donadío, Lucía
Muchnik de Lederkremer, Rosa María
Gallo, Carola
author_facet Gandolfi Donadío, Lucía
Muchnik de Lederkremer, Rosa María
Gallo, Carola
author_sort Gandolfi Donadío, Lucía
title Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
title_short Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
title_full Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
title_fullStr Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
title_full_unstemmed Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
title_sort synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
publishDate 2011
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v9_n7_p2085_GandolfiDonadio
http://hdl.handle.net/20.500.12110/paper_14770520_v9_n7_p2085_GandolfiDonadio
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AT gallocarola synthesisofarabinofuranosebranchedgalactofurantetrasaccharidesconstituentsofmycobacterialarabinogalactan
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