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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Autor principal:	Kovensky, José Eduardo
Publicado:	1999
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v64_n17_p6202_Kovensky http://hdl.handle.net/20.500.12110/paper_00223263_v64_n17_p6202_Kovensky
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00223263_v64_n17_p6202_Kovensky
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spelling	paper:paper_00223263_v64_n17_p6202_Kovensky2023-06-08T14:49:30Z D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose Kovensky, José Eduardo 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. 1999 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v64_n17_p6202_Kovensky 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, José Eduardo 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.
author	Kovensky, José Eduardo
author_facet	Kovensky, José Eduardo
author_sort	Kovensky, José Eduardo
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
publishDate	1999
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v64_n17_p6202_Kovensky http://hdl.handle.net/20.500.12110/paper_00223263_v64_n17_p6202_Kovensky
work_keys_str_mv	AT kovenskyjoseeduardo dgalactofuranosylphosphonatesfirstsynthesisofudpcdgalactofuranose
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D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose

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