Abstract:
The first synthesis of methyl β-d-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of l-altrofuranose (16) or d-galactofuranose (18) as the reducing end, are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf found in glycoconjugates of many pathogenic microorganisms. The conformational preferences of 16 and 18 in solution were assessed by means of molecular modeling and NMR techniques. These thiodisaccharides have been evaluated as inhibitors of the β-d-galactofuranosidase from Penicillium fellutanum. The kinetics of the inhibition showed that they behave as competitive inhibitors. As expected, compound 18 (Ki = 0.15 mM), with the same configuration for the reducing end as the natural substrate of the enzyme, was a stronger inhibitor than 16 (Ki = 2.23 mM). This journal is © The Royal Society of Chemistry 2015.
Registro:
Documento: |
Artículo
|
Título: | Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase |
Autor: | Lo Fiego, M.J.; Marino, C.; Varela, O. |
Filiación: | CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina INQUISUR-CONICET, Departamento de Química, Universidad Nacional Del sur, Avenida Alem 1253, Bahía Blanca, 8000, Argentina
|
Palabras clave: | Conformational preferences; Galactofuranose; Glycoconjugates; Glycomimetics; Natural substrates; NMR techniques; Pathogenic microorganisms; Reducing ends; Microorganisms |
Año: | 2015
|
Volumen: | 5
|
Número: | 57
|
Página de inicio: | 45631
|
Página de fin: | 45640
|
DOI: |
http://dx.doi.org/10.1039/c5ra06899a |
Título revista: | RSC Advances
|
Título revista abreviado: | RSC Adv.
|
ISSN: | 20462069
|
CODEN: | RSCAC
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n57_p45631_LoFiego |
Referencias:
- Renaudet, O., Dumy, P., (2008) Tetrahedron, 58, pp. 2127-2135
- Arjona, O., Gómez, A.M., López, J.C., Plumet, J., (2007) Chem. Rev., 107, pp. 1919-2036
- Robina, I., Vogel, P., (2005) Synthesis, 5, pp. 675-702
- Yuan, X., Linhardt, R.J., (2005) Curr. Top. Med. Chem., 5, pp. 1393-1430
- Varky, A., (1993) Glycobiology, 3, pp. 97-130
- Dwek, R.A., (1996) Chem. Rev., 96, pp. 683-720
- Dube, D.H., Bertozzi, C.R., (2005) Nat. Rev. Drug Discovery, 4, pp. 477-488
- Driguez, H., (2001) ChemBioChem, 2, pp. 311-318
- Defaye, J., Gelas, J., (1991) Studies in Natural Product Chemistry, 8, pp. 315-357. , ed. A. U. Rahman, Elsevier
- Driguez, H., (1997) Top. Curr. Chem., 187, pp. 85-116
- Szilágyi, L., Varela, O., (2006) Curr. Org. Chem., 10, pp. 1745-1770
- Pachamuthu, K., Schmidt, R.R., (2006) Chem. Rev., 106, pp. 160-187
- Uhrig, M.L., Manzano, V.E., Varela, O., (2006) Eur. J. Org. Chem., pp. 162-168
- Uhrig, M.L., Szilágyi, L., Kovér, K.E., Varela, O., (2007) Carbohydr. Res., 342, pp. 1841-1849
- Cagnoni, A.J., Uhrig, M.L., Varela, O., (2009) Bioorg. Med. Chem., 17, pp. 6203-6212
- Manzano, V.E., Uhrig, M.L., Varela, O., (2008) J. Org. Chem., 73, pp. 7224-7235
- Manzano, V.E., Uhrig, M.L., Varela, O., (2012) Org. Biomol. Chem., 10, pp. 8884-8894
- Repetto, E., Manzano, V.E., Uhrig, M.L., Varela, O., (2012) J. Org. Chem., 77, pp. 253-265
- Repetto, E., Marino, C., Uhrig, M.L., Varela, O., (2008) Eur. J. Org. Chem., pp. 540-547
- Repetto, E., Marino, C., Uhrig, M.L., Varela, O., (2009) Bioorg. Med. Chem., 17, pp. 2703-2711
- Repetto, E., Marino, C., Varela, O., (2013) Bioorg. Med. Chem., 21, pp. 3327-3333
- Randell, K.D., Johnston, B.D., Lee, E.E., Pinto, B.M., (2000) Tetrahedron: Asymmetry, 11, pp. 207-222
- Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552
- Richards, M.R., Lowary, T.L., (2009) ChemBioChem, 10, pp. 1920-1938
- Pedersen, L.L., Turco, S., (2003) Cell. Mol. Life Sci., 60, pp. 259-266
- Peltier, P., Euzen, R., Daniellou, R., Nugier-Chauvin, C., Ferrières, V., (2008) Carbohydr. Res., 343, pp. 1897-1923
- Marino, C., Gallo-Rodriguez, C., Lederkremer, R.M., (2012) Glycans: Biochemistry, Characterization and Applications, pp. 207-268. , ed. H. M. Mora-Montes, Nova Science Publishers
- Tefsen, B., Ram, A.F., Van Die, I., Routier, F.H., (2012) Glycobiology, 22, pp. 456-469
- Kremer, L., Dover, L.G., Morehouse, C., Hitchin, P., Everett, M., Morris, H.R., Dell, A., Besra, G.S., (2001) J. Biol. Chem., 276, pp. 26430-26440
- Nassau, P.M., Martin, S.L., Brown, R.E., Weston, A., Monsey, D., McNeil, M.R., Duncan, K., (1996) J. Bacteriol., 178, pp. 1047-1052
- Sanders, D.A.R., Staines, A.G., McMahon, S.A., McNeil, M.R., Whitfield, C., Naismith, J.H., (2001) Nat. Struct. Biol., 8, pp. 858-863
- Wesener, D.A., May, J.F., Huffman, E.M., Kiessling, L.L., (2013) Biochemistry, 52, pp. 4391-4398
- Marino, C., Baldoni, L., (2014) ChemBioChem, 15, pp. 188-2014
- Imamura, A., Lowary, T., (2011) Trends Glycosci. Glycotechnol., 23, pp. 134-152
- Rietschel-Berst, M., Jentoft, N.H., Rick, P.D., Pletcher, C., Fang, F., Gander, J.E., (1977) J. Biol. Chem., 252, pp. 3219-3226
- Daley, L.S., Ströbel, G.A., (1983) Plant Sci. Lett., 30, pp. 145-154
- Cousin, M.A., Notermans, S., Hoogerhout, P., Van Boom, J.H., (1989) J. Appl. Bacteriol., 66, pp. 311-317
- Wallis, G.-L., Hemming, F.W., Pederby, J.F., (2001) Biochim. Biophys. Acta, 1525, pp. 19-28
- Golgher, D.B., Colli, W., Souto-Padron, T., Zingales, B., (1993) Mol. Biochem. Parasitol., 60, pp. 249-264
- Miletti, L.C., Mariño, K., Marino, C., Colli, W., Alves, M.J.M., Lederkremer, R.M., (2003) Mol. Biochem. Parasitol., 127, pp. 85-88
- Bordoni, A., Lederkremer, R.M., Marino, C., (2010) Bioorg. Med. Chem., 18, pp. 5339-5345
- Bordoni, A., Lima, C., Mariño, K., Lederkremer, R.M., Marino, C., (2008) Carbohydr. Res., 343, pp. 1863-1869
- Gallo-Rodriguez, C., Gandolfi, L., Lederkremer, R.M., (1999) Org. Lett., 1, pp. 245-247
- Horton, D., Priebe, W., Varela, O., (1985) Carbohydr. Res., 144, pp. 325-331
- Zunszain, P.A., Varela, O., (1995) J. Chem. Res., Synop., pp. 486-487
- Praly, J.-P., Lemieux, R.U., (1987) Can. J. Chem., 65, pp. 213-223
- Marino, C., Mariño, K., Miletti, L., Manso Alves, M.J., Colli, W., Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904
- Mariño, K., Marino, C., (2005) ARKIVOC, 12, pp. 341-351
- Peters, T., Pinto, B.M., (1998) Curr. Opin. Struct. Biol., 6, pp. 710-720
- Imberty, A., (1997) Curr. Opin. Struct. Biol., 7, pp. 617-623
- Jiménez-Barbero, J., Asensio, J.L., Cañana, J., Poveda, A., (1999) Curr. Opin. Struct. Biol., 9, pp. 549-555
- García-Herrero, A.E., Montero Muñoz, J.L., Espinosa, J.F., Vián, A., García, J.L., Asensio, J.L., Cañada, F.J., Jiménez-Barbero, J., (2002) J. Am. Chem. Soc., 124, pp. 4804-4810
- Bonas, G., Vignon, M.R., (1991) Carbohydr. Res., 211, pp. 191-205
- Javaroni, F., Ferreira, A.B.B., Da Silva, C.O., (2009) Carbohydr. Res., 344, pp. 1235-1247
- Grachev, A.A., Gerbst, A.G., Gening, M.L., Titov, D.V., Yudina, O.N., Tsetkov, Y.E., Shashkov, A.S., Nifantiev, N.E., (2011) Carbohydr. Res., 346, pp. 2499-2510
- Dabrowski, J., Kožár, T., Grosskurth, H., Nifant'Ev, N.E., (1995) J. Am. Chem. Soc., 117, pp. 5534-5539
- Taha, H.A., Richards, M.R., Lowary, T.L., (2012) Chem. Rev., 113, pp. 1851-1876
Citas:
---------- APA ----------
Lo Fiego, M.J., Marino, C. & Varela, O.
(2015)
. Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase. RSC Advances, 5(57), 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a---------- CHICAGO ----------
Lo Fiego, M.J., Marino, C., Varela, O.
"Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase"
. RSC Advances 5, no. 57
(2015) : 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a---------- MLA ----------
Lo Fiego, M.J., Marino, C., Varela, O.
"Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase"
. RSC Advances, vol. 5, no. 57, 2015, pp. 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a---------- VANCOUVER ----------
Lo Fiego, M.J., Marino, C., Varela, O. Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase. RSC Adv. 2015;5(57):45631-45640.
http://dx.doi.org/10.1039/c5ra06899a