Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis
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. Th...
Guardado en:
| Autores principales: | , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00084042_v84_n4_p486_GandolfiDonadio |
| Aporte de: |
| id |
todo:paper_00084042_v84_n4_p486_GandolfiDonadio |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_00084042_v84_n4_p486_GandolfiDonadio2023-10-03T14:05:59Z Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis Gandolfi-Donadío, L. Gallo-Rodriguez, C. De Lederkremer, R.M. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00084042_v84_n4_p486_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 |
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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Gandolfi-Donadío, L. Gallo-Rodriguez, C. De Lederkremer, R.M. |
| author_facet |
Gandolfi-Donadío, L. Gallo-Rodriguez, C. De Lederkremer, R.M. |
| author_sort |
Gandolfi-Donadío, L. |
| title |
Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis |
| title_short |
Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis |
| title_full |
Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis |
| title_fullStr |
Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis |
| title_full_unstemmed |
Facile synthesis of α-D-Araf-(1→5)-D-Galf, the linker unit of the arabinan to the galactan in Mycobacterium tuberculosis |
| title_sort |
facile synthesis of α-d-araf-(1→5)-d-galf, the linker unit of the arabinan to the galactan in mycobacterium tuberculosis |
| url |
http://hdl.handle.net/20.500.12110/paper_00084042_v84_n4_p486_GandolfiDonadio |
| work_keys_str_mv |
AT gandolfidonadiol facilesynthesisofadaraf15dgalfthelinkerunitofthearabinantothegalactaninmycobacteriumtuberculosis AT gallorodriguezc facilesynthesisofadaraf15dgalfthelinkerunitofthearabinantothegalactaninmycobacteriumtuberculosis AT delederkremerrm facilesynthesisofadaraf15dgalfthelinkerunitofthearabinantothegalactaninmycobacteriumtuberculosis |
| _version_ |
1807316120190844928 |