D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose
The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the α-phosphono analogue has been easily converted int...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00223263_v64_n17_p6202_Kovensky |
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todo:paper_00223263_v64_n17_p6202_Kovensky2023-10-03T14:31:22Z D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose Kovensky, J. McNeil, M. Sinaÿ, P. antimycobacterial agent dextro galactofuranose enzyme inhibitor monosaccharide mutase phosphonic acid derivative unclassified drug uridine diphosphate c dextro galactofuranose article Chagas disease controlled study crystallization drug synthesis enzyme inhibition escherichia coli mycobacterium tuberculosis nonhuman nuclear magnetic resonance trypanosoma cruzi The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the α-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP- galactopyranose mutase crystallization studies. Fil:Kovensky, J. 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_00223263_v64_n17_p6202_Kovensky |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
antimycobacterial agent dextro galactofuranose enzyme inhibitor monosaccharide mutase phosphonic acid derivative unclassified drug uridine diphosphate c dextro galactofuranose article Chagas disease controlled study crystallization drug synthesis enzyme inhibition escherichia coli mycobacterium tuberculosis nonhuman nuclear magnetic resonance trypanosoma cruzi |
| spellingShingle |
antimycobacterial agent dextro galactofuranose enzyme inhibitor monosaccharide mutase phosphonic acid derivative unclassified drug uridine diphosphate c dextro galactofuranose article Chagas disease controlled study crystallization drug synthesis enzyme inhibition escherichia coli mycobacterium tuberculosis nonhuman nuclear magnetic resonance trypanosoma cruzi Kovensky, J. McNeil, M. Sinaÿ, P. D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| topic_facet |
antimycobacterial agent dextro galactofuranose enzyme inhibitor monosaccharide mutase phosphonic acid derivative unclassified drug uridine diphosphate c dextro galactofuranose article Chagas disease controlled study crystallization drug synthesis enzyme inhibition escherichia coli mycobacterium tuberculosis nonhuman nuclear magnetic resonance trypanosoma cruzi |
| description |
The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the α-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP- galactopyranose mutase crystallization studies. |
| format |
JOUR |
| author |
Kovensky, J. McNeil, M. Sinaÿ, P. |
| author_facet |
Kovensky, J. McNeil, M. Sinaÿ, P. |
| author_sort |
Kovensky, J. |
| title |
D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| title_short |
D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| title_full |
D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| title_fullStr |
D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| title_full_unstemmed |
D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose |
| title_sort |
d-galactofuranosylphosphonates. first synthesis of udp-c-d- galactofuranose |
| url |
http://hdl.handle.net/20.500.12110/paper_00223263_v64_n17_p6202_Kovensky |
| work_keys_str_mv |
AT kovenskyj dgalactofuranosylphosphonatesfirstsynthesisofudpcdgalactofuranose AT mcneilm dgalactofuranosylphosphonatesfirstsynthesisofudpcdgalactofuranose AT sinayp dgalactofuranosylphosphonatesfirstsynthesisofudpcdgalactofuranose |
| _version_ |
1807321974953738240 |