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Abstract:

β-D-galactofuranosidase is a good chemotherapeutic target for the design of inhibitors, since β-D-galactofuranose is a constituent of important parasite glycoconjugates but is not present in the host mammals. With this aim, we have synthesized for the first time alkyl, benzyl and aryl 1-thio-β-D-galactofuranosides by condensation of pent-O-benzoyl-α,β-D-galactofuranose with the corresponding thiols, in the presence of SnCl4 as catalyst. The complete chemical and spectroscopical characterization of these compounds showed that the reaction was stereoselective. Debenzoylation with sodium methoxide afforded the β-S-galactofuranosides in high yield. The thioglycosides were tested as inhibitors of the β-D-galactofuranosidase of Penicillium fellutanum, using for the first time 4-nitrophenyl-β-D-galactofuranoside as chromogenic substrate. The 4-aminophenyl-1-thio-β-D-galactofuranoside, obtained by catalytic hydrogenation of the nitrophenyl derivative, was the best inhibitor being then an adequate ligand for the preparation of an affinity phase aimed at the isolation of β-D-galactofuranosidases from different sources. Also the inhibitory activity of D-galactono-1,4-lactone was shown.

Registro:

Documento: Artículo
Título:1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors
Autor:Marino, C.; Mariño, K.; Miletti, L.; Alves, M.J.M.; Colli, W.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Depto. de Quim. Orgánica, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina
Instituto de Química, Departamento de Bioquímica, Universidade de São Paulo, CP 260777, CEP05599-970, PP, Brazil
Palabras clave:Affinity ligands; Galactofuranose; Galactofuranosidase inhibitors; thio-β-D-galactofuranosides; galactofuranosidase; galactofuranoside derivative; unclassified drug; affinity chromatography; article; controlled study; drug synthesis; enzyme isolation; hydrogenation; nonhuman; priority journal; stereochemistry; Mammalia; Penicillium fellutanum
Año:1998
Volumen:8
Número:9
Página de inicio:901
Página de fin:904
DOI: http://dx.doi.org/10.1093/glycob/8.9.901
Título revista:Glycobiology
Título revista abreviado:Glycobiology
ISSN:09596658
CODEN:GLYCE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09596658_v8_n9_p901_Marino

Referencias:

  • Acosta Serrano, A., Schenkman, S., Yoshida, N., Mehlert, A., Richardson, J.M., Ferguson, M.A.J., The lipid structure of the glycosylphosphatictylinositol-anchored mucin-like sialic acid acceptors of Trypanosoma cruzi changes during parasite differenciation from epimastigotes to infective metacyclic trypomastigote forms (1995) J. Biol. Chem., 270, pp. 27244-27253
  • Blanc-Muesser, M., Defaye, J., Driguez, H., Syntheses stereoselectives de 1-thioglycosides (1978) Carbohydr. Res., 67, pp. 305-328
  • Bock, K., Pedersen, C., Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides (1983) Adv. Carbohydr. Chem., 41, pp. 27-66
  • Bradford, M., A rapid and sensitive method for the quantification of protein utilizing the principle of protein-dye binding (1976) Anal. Biochem., 72, pp. 248-254
  • Daffe, M., Brennan, P.J., Mc.Neil, M., Predominant structural features of cell wall arabinogalactan of Mycobacterium tuberculosis as revealed through characterization of oligoglycosyl alditol fragments by gas chromatography/mass spectrometry and by 1H and 13C NMR analyses (1990) J. Biol. Chem., 265, pp. 6734-6743
  • Daley, L.S., Strobel, G.A., β-galactofuranosidase activity in Helminthosporium sacchari and its relationship to the production of helminthosporoside (1983) Plant Sci. Lett., 30, pp. 145-154
  • Ferrier, R.J., Furneaux, R.H., 1,2-trans-1-Thioglycosides (1980) Methods Carbohydr. Chem., 8, pp. 251-253
  • Garegg, P.J., Thioglycosides as glycosyl donors in oligosaccharide synthesis (1997) Adv. Carbohydr. Chem. Biochem., 52, pp. 179-205
  • Lederkremer, R.M., Casal, O.L., Alves, M.J.M., Colli, W., Evidence for the presence of D-galactofuranose in the lipopeptidophosphoglycan from Trypanosoma cruzi (1980) FEBS Lett., 116, pp. 25-29
  • Lederkremer, R.M., Colli, W., Galactofuranose containing glycoconjugates in trypanosomatids (1995) Glycobiology, 5, pp. 547-552
  • Lederkremer, R.M., Marino, C., Varela, O., Convenient synthesis of 5-O-and 3,5-di-O-(β-D-galactofuranosyl)-D-galactofuranose (1990) Carbohydr. Res., 200, pp. 227-235
  • Lederkremer, R.M., Lima, C., Ramirez, M.I., Ferguson, M.A.J., Homans, S.W., Thomas-Oates, J., Complete structure of the glycan of lipopeptidophosphoglycan from Trypanosoma cruzi epimastigotes (1991) J. Biol. Chem., 266, pp. 23670-23675
  • Levvy, G.A., Hay, A.J., Conchie, J., Inhibition of glycosidases by aldonolactones of corresponding configuration. 4 . Inhibitors of mannosidase and glucosidase (1964) Biochem. J., 91, pp. 378-384
  • Marino, C., Varela, O., Lederkremer, R.M., Synthesis of galactofuranose disaccharides of biological significance (1989) Carbohydr. Res., 190, pp. 65-76
  • Marino, C., Varela, O., Lederkremer, R.M., Synthesis of 4-methylcoumarin-7-yl-β-D-galactofuranosidase, a fluorogenic substrate for galactofuranosidase (1995) Carbohydr. Res., 276, pp. 209-213
  • Miller, A.L., Frost, R.G., O'Brien, J.S., Purified human liver acid β-D-galactosidases possessing activity towards GM1-ganglioside and lactosylceramide (1977) Biochem. J., 165, pp. 591-594
  • Osumi, K., Enamoto, M., Sugimura, H., Stereoselective synthesis of α-D-galactofuranosides by the N-bromoimide-promoted glycosylation using O-benzylated-1-thiogalactofuranoside (1996) Carbohydr. Lett., 2, pp. 35-38
  • Pazur, J.H., Affinity chromatography of macromolecular substances on adsorbents bearing carbohydrate ligands (1981) Adv. Carbohydr. Chem. Biochem., 39, pp. 405-447
  • Preston, J.F., Gander, J.E., Isolation and partial characterization of the extracellular polysaccharides of Penicillium charlesii (1968) Arch. Biochem. Biophys., 124, pp. 504-512
  • Previato, J.O., Jones, C., Gonçalves, L.P.B., Wait, R., Travassos, L.R., Mendonça-Previato, L., O-Glycosidically linked N-acetylglucosamine bound oligosaccharides from glycoproteins of Trypanosoma cruzi (1994) Biochem. J., 301, pp. 151-159
  • Previato, J.O., Jones, C., Xavier, M.T., Wait, R., Travassos, L.R., Parodi, A.J., Mendonça-Previato, L., Stuctural characterization of the major glycosylphosphatidylinositol membrane-anchored glycoprotein from epimastigote forms of Trypanosoma cruzi Y-strain (1995) J. Biol. Chem., 270, pp. 7241-7250
  • Rietschel-Berst, M., Jentoft, N.H., Rick, P.D., Pletcher, C., Fang, F., Gander, J.E., Extracellular exo-β-galactofuranosidase from Penicillium charlesii (1977) J. Biol. Chem., 252, pp. 3219-3226
  • Steers, E., Cuatrecasas, P., Pollard, H.B., The purification of β-galactosidase from E. coli by affinity chromatography (1971) J. Biol. Chem., 246, pp. 196-200
  • Tropper, F.D., Andersson, F.O., Grand-Maître, C., Roy, R., Phase transfer catalyzed synthesis of 4-nitrophenyl-1-thio-β-D-glycobiosides (1992) Carbohydr. Res., 229, pp. 149-154
  • Turco, S.J., Descoteaux, A., The lipophosphoglycan of Leishmania parasites (1992) Annu. Rev. Microbiol., 46, pp. 65-94
  • Varela, O., Marino, C., Lederkremer, R.M., Synthesis of p-nitrophenyl β-D-galactofuranoside. A convenient substrate for β-D-galactofuranosidase (1986) Carbohydr. Res., 155, pp. 247-251
  • Wallenfels, K., Malhotra, O.P., Galactosidases (1961) Adv. Carbohydr. Chem., 16, pp. 239-298
  • Whitfield, C., Richards, J.C., Perry, M.B., Clarke, B.R., Mac Lean, L.L., Expression of two structurally distinct D-galactan O antigens in the lipopolysaccharide of Klebsiella pneumoniae serotype O1 (1991) J. Bacteriol., 173, pp. 1420-1431
  • Wolfrom, M.L., Yosizawa, Z., Juliano, B.O., Ethyl 1-thio-α-D-galactofuranoside (1959) J. Org. Chem., 24, pp. 1529-1530
  • Zunszain, P.A., Varela, O., A comparative study on the conformation of derivatives of furanoses, 4-thiofuranoses and C-, N- and S-furanosides (1995) J. Chem. Res., pp. 486-487

Citas:

---------- APA ----------
Marino, C., Mariño, K., Miletti, L., Alves, M.J.M., Colli, W. & De Lederkremer, R.M. (1998) . 1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors. Glycobiology, 8(9), 901-904.
http://dx.doi.org/10.1093/glycob/8.9.901
---------- CHICAGO ----------
Marino, C., Mariño, K., Miletti, L., Alves, M.J.M., Colli, W., De Lederkremer, R.M. "1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors" . Glycobiology 8, no. 9 (1998) : 901-904.
http://dx.doi.org/10.1093/glycob/8.9.901
---------- MLA ----------
Marino, C., Mariño, K., Miletti, L., Alves, M.J.M., Colli, W., De Lederkremer, R.M. "1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors" . Glycobiology, vol. 8, no. 9, 1998, pp. 901-904.
http://dx.doi.org/10.1093/glycob/8.9.901
---------- VANCOUVER ----------
Marino, C., Mariño, K., Miletti, L., Alves, M.J.M., Colli, W., De Lederkremer, R.M. 1-Thio-β-D-galactofuranosides: Synthesis and evaluation as β-D-galactofuranosidase inhibitors. Glycobiology. 1998;8(9):901-904.
http://dx.doi.org/10.1093/glycob/8.9.901