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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todo:paper_14770520_v9_n7_p2085_GandolfiDonadio2023-10-03T16:19:08Z Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan Gandolfi-Donadío, L. Santos, M. De Lederkremer, R.M. Gallo-Rodriguez, C. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, L. Santos, M. De Lederkremer, R.M. Gallo-Rodriguez, C. 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. |
| format |
JOUR |
| author |
Gandolfi-Donadío, L. Santos, M. De Lederkremer, R.M. Gallo-Rodriguez, C. |
| author_facet |
Gandolfi-Donadío, L. Santos, M. De Lederkremer, R.M. Gallo-Rodriguez, C. |
| author_sort |
Gandolfi-Donadío, L. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_14770520_v9_n7_p2085_GandolfiDonadio |
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