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
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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
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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
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Volumen: | 64
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Número: | 17
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Página de inicio: | 6202
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Página de fin: | 6205
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DOI: |
http://dx.doi.org/10.1021/jo990196p |
Título revista: | Journal of Organic Chemistry
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Título revista abreviado: | J. Org. Chem.
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ISSN: | 00223263
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CODEN: | JOCEA
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CAS: | mutase, 9047-56-7
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v64_n17_p6202_Kovensky |
Referencias:
- De Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, p. 547
- De Arruda, M.V., Colli, W., Zingales, B., (1989) Eur. J. Biochem., 182, p. 413
- Nassau, P., Martin, S., Brown, R., Weston, A., Monsey, D., McNeil, M., Duncan, K., (1996) J. Bacteriol., 178, p. 1047
- Lee, R., Monsey, D., Weston, A., Duncan, K., Rithner, C., McNeil, M., (1996) Anal. Biochem., 242, p. 1
- Koplin, R., Brisson, J.R., Whitfield, C., (1997) J. Biol. Chem., 272, p. 4121
- De Lederkremer, R.M., Nahmad, V.B., Varela, O., (1994) J. Org. Chem., 59, p. 690
- Marino, C., Varela, O., De Lederkremer, R.M., (1989) Carbohydr. Res., 190, p. 65
- Nicotra, F., Panza, L., Ronchetti, F., Russo, G., Toma, L., (1987) Carbohydr. Res., 171, p. 49
- Houlton, J.S., Motherwell, W.B., Ross, B.C., Tozer, M.J., Williams, D.J., Slawin, A.M.Z., (1993) Tetrahedron, 49, p. 8087
- Piettre, S.R., (1996) Tetrahedron Lett., 37, p. 2233
- Fleet, G.W.J., Son, J.C., (1988) Tetrahedron, 44, p. 2637
- Iwashige, T., Saeki, H., (1967) Chem. Pharm. Bull. (Tokyo), 15, p. 1803
- Decoster, E., Lacombe, J.-M., Strebler, J.-L., Ferrari, B., Pavia, A., (1983) J. Carbohydr. Chem., 2, p. 329
- Weston, A., Stern, R.J., Lee, R.E., Nassau, P.M., Monsey, D., Martin, S.L., Scherman, M.S., McNeil, M.R., (1998) Tuberc. Lung Dis., 78, p. 123
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