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Abstract:

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.

Registro:

Documento: Artículo
Título:D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose
Autor:Kovensky, J.; McNeil, M.; Sinaÿ, P.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, Pab. II, 3er. piso, 1428 Buenos Aires, Argentina
Department of Microbiology, Colorado State University, Fort Collins, CO 80523, United States
Ecole Normale Supérieure, Département de Chimie, URA 1686, 24 rue Lhomond, 75231 Paris Cédex 05, France
Palabras clave: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
Año:1999
Volumen:64
Número:17
Página de inicio:6202
Página de fin:6205
DOI: http://dx.doi.org/10.1021/jo990196p
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:mutase, 9047-56-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v64_n17_p6202_Kovensky

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Citas:

---------- APA ----------
Kovensky, J., McNeil, M. & Sinaÿ, P. (1999) . D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose. Journal of Organic Chemistry, 64(17), 6202-6205.
http://dx.doi.org/10.1021/jo990196p
---------- CHICAGO ----------
Kovensky, J., McNeil, M., Sinaÿ, P. "D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose" . Journal of Organic Chemistry 64, no. 17 (1999) : 6202-6205.
http://dx.doi.org/10.1021/jo990196p
---------- MLA ----------
Kovensky, J., McNeil, M., Sinaÿ, P. "D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose" . Journal of Organic Chemistry, vol. 64, no. 17, 1999, pp. 6202-6205.
http://dx.doi.org/10.1021/jo990196p
---------- VANCOUVER ----------
Kovensky, J., McNeil, M., Sinaÿ, P. D-galactofuranosylphosphonates. First synthesis of UDP-C-D- galactofuranose. J. Org. Chem. 1999;64(17):6202-6205.
http://dx.doi.org/10.1021/jo990196p