Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis
The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec...
| Autores principales: | , , |
|---|---|
| Publicado: |
2003
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v68_n18_p6928_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v68_n18_p6928_GandolfiDonadio |
| Aporte de: |
| id |
paper:paper_00223263_v68_n18_p6928_GandolfiDonadio |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_00223263_v68_n18_p6928_GandolfiDonadio2023-06-08T14:49:34Z Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Glycosylation Bacteria Immunology Synthesis (chemical) Organic compounds acetamide derivative beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) dextro galactofuranose beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) beta dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) beta dextro galactofuranose furanone derivative galactan galactofuranosyltransferase lactone derivative transferase trisaccharide unclassified drug article bacterial cell wall chemical modification glycosylation Mycobacterium tuberculosis substitution reaction synthesis Carbohydrate Sequence Chromatography, Thin Layer Furans Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Sequence Data Mycobacterium tuberculosis Stereoisomerism Trisaccharides Triterpenes The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl β-D-Galf-(1→6)-β-D-Galf-(1→ 5)-β-D-Galf (2) and dec-9-enyl β-D-Galf-(1→5)-β -D-Galf-(1→6)-β-D Galf (9) so far reported as convenient substrates for the galactofuranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation. Fil:Gandolfi-Donadío, L. 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. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2003 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v68_n18_p6928_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v68_n18_p6928_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 |
Glycosylation Bacteria Immunology Synthesis (chemical) Organic compounds acetamide derivative beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) dextro galactofuranose beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) beta dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) beta dextro galactofuranose furanone derivative galactan galactofuranosyltransferase lactone derivative transferase trisaccharide unclassified drug article bacterial cell wall chemical modification glycosylation Mycobacterium tuberculosis substitution reaction synthesis Carbohydrate Sequence Chromatography, Thin Layer Furans Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Sequence Data Mycobacterium tuberculosis Stereoisomerism Trisaccharides Triterpenes |
| spellingShingle |
Glycosylation Bacteria Immunology Synthesis (chemical) Organic compounds acetamide derivative beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) dextro galactofuranose beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) beta dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) beta dextro galactofuranose furanone derivative galactan galactofuranosyltransferase lactone derivative transferase trisaccharide unclassified drug article bacterial cell wall chemical modification glycosylation Mycobacterium tuberculosis substitution reaction synthesis Carbohydrate Sequence Chromatography, Thin Layer Furans Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Sequence Data Mycobacterium tuberculosis Stereoisomerism Trisaccharides Triterpenes Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| topic_facet |
Glycosylation Bacteria Immunology Synthesis (chemical) Organic compounds acetamide derivative beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) dextro galactofuranose beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-5) beta dextro galactofuranose(1-6) beta dextro galactofuranose dec 9 enyl beta dextro galactofuranose(1-6) beta dextro galactofuranose(1-5) beta dextro galactofuranose furanone derivative galactan galactofuranosyltransferase lactone derivative transferase trisaccharide unclassified drug article bacterial cell wall chemical modification glycosylation Mycobacterium tuberculosis substitution reaction synthesis Carbohydrate Sequence Chromatography, Thin Layer Furans Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Sequence Data Mycobacterium tuberculosis Stereoisomerism Trisaccharides Triterpenes |
| description |
The galactofuran is a crucial constituent of the cell wall of mycobacteria. An efficient synthesis of the two trisaccharide units of the galactan is described. The strategy relies on the use of substituted D-galactono-1,4-lactones as precursors for the internal and the reducing galactofuranoses. Dec-9-enyl β-D-Galf-(1→6)-β-D-Galf-(1→ 5)-β-D-Galf (2) and dec-9-enyl β-D-Galf-(1→5)-β -D-Galf-(1→6)-β-D Galf (9) so far reported as convenient substrates for the galactofuranosyl transferase, and possibly useful for immunological studies, were obtained by the trichloroacetimidate method of glycosylation. |
| author |
Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María |
| author_facet |
Gandolfi Donadío, Lucía Gallo, Carola Muchnik de Lederkremer, Rosa María |
| author_sort |
Gandolfi Donadío, Lucía |
| title |
Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| title_short |
Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| title_full |
Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| title_fullStr |
Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| title_full_unstemmed |
Syntheses of β-D-Galf-(1→6)-β-D-Galf-(1→5)-D-Galf and β-D-Galf-(1→5)-β-D-Galf-(1→6)-D-Galf, trisaccharide units in the galactan of Mycobacterium tuberculosis |
| title_sort |
syntheses of β-d-galf-(1→6)-β-d-galf-(1→5)-d-galf and β-d-galf-(1→5)-β-d-galf-(1→6)-d-galf, trisaccharide units in the galactan of mycobacterium tuberculosis |
| publishDate |
2003 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v68_n18_p6928_GandolfiDonadio http://hdl.handle.net/20.500.12110/paper_00223263_v68_n18_p6928_GandolfiDonadio |
| work_keys_str_mv |
AT gandolfidonadiolucia synthesesofbdgalf16bdgalf15dgalfandbdgalf15bdgalf16dgalftrisaccharideunitsinthegalactanofmycobacteriumtuberculosis AT gallocarola synthesesofbdgalf16bdgalf15dgalfandbdgalf15bdgalf16dgalftrisaccharideunitsinthegalactanofmycobacteriumtuberculosis AT muchnikdelederkremerrosamaria synthesesofbdgalf16bdgalf15dgalfandbdgalf15bdgalf16dgalftrisaccharideunitsinthegalactanofmycobacteriumtuberculosis |
| _version_ |
1768546617506398208 |