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Abstract:

The synthesis of free β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc and the corresponding alditol which has been previously isolated by reductive β-elimination of Trypanosoma cruzi glycoproteins are described. A convergent route was envisioned by condensing an acceptor derivative of β-D-Galf-(1→4)-D-GlcNAc with a donor derivative of β-D-Galp-(1→3)-D-Galp. The trichloroacetimidate method, as well as SnCl4-promoted condensation were utilized for the introduction of the galactofuranosyl unit. On the other hand, the glycosyl-aldonolactone approach, followed by reduction of the lactone with diisoamylborane, and further isomerization to the galactopyranose configuration gave the donor derivative, which was condensed by the trichloroacetimidate method. Moreover, a synthon for the introduction of the β-D-Galp-(1→3)-D-Galf unit is described. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi
Autor:Gallo-Rodriguez, C.; Gil-Libarona, M.A.; Mendoza, V.M.; de Lederkremer, R.M.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:D-galactono-1,4-lactone; Galactofuranose; Glycosylation; Mucins; Trichloroacetimidate; Trypanosoma cruzi; beta dextro galactopyranose (1-3) beta dextro galactopyranose (1-6) [beta dextro galactofuranose (1-4)] dextro n acetylglucosamine; mucin; polysaccharide; unclassified drug; article; conformation; elimination reaction; isomerism; nonhuman; polymerization; priority journal; reduction; synthesis; Trypanosoma cruzi; Trypanosoma; Trypanosoma cruzi
Año:2002
Volumen:58
Número:46
Página de inicio:9373
Página de fin:9380
DOI: http://dx.doi.org/10.1016/S0040-4020(02)01226-7
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v58_n46_p9373_GalloRodriguez

Referencias:

  • Previato, J.O., Jones, C., Gonçalves, L.P.B., Wait, R., Travassos, L.R., Mendonça-Previato, L., (1994) Biochem. J., 300, pp. 151-159
  • Acosta Serrano, A., Schenkman, S., Yoshida, N., Mehlert, A., Richardson, J., Ferguson, M.A.J., (1995) J. Biol. Chem., 270, pp. 27244-27253
  • Previato, J.O., Jones, C., Xavier, M.T., Wait, R., Travassos, L.R., Parodi, A.J., Mendonça-Previato, L., (1995) J. Biol. Chem., 270, pp. 7241-7250
  • Pollevick, G.D., Di Noia, J.M., Salto, M.L., Lima, C., Leguizamon, M.S., Lederkremer, R.M., Frasch, A.C.C., (2000) J. Biol. Chem., 275, pp. 27671-27680
  • Todeschini, A.R., Xavier da Silveira, E., Jones, C., Wait, R., Previato, J.O., Mendonça-Previato, L., (2001) Glycobiology, 11, pp. 47-55
  • Schenkman, S., Eichinger, D., Pereira, M.E.A., Nussenzweig, V., (1994) Annu. Rev. Microbiol., 48, pp. 499-523
  • Parodi, A.J., Pollevick, G.D., Mautner, M., Buschiazzo, A., Sanchez, D.O., Frasch, A.C.C., (1992) EMBO J., 11, pp. 1705-1710
  • Salto, M.L., Gallo-Rodriguez, C., Lima, C., Lederkremer, R.M., (2000) Anal. Biochem., 279, pp. 79-84
  • Gallo-Rodriguez, C., Varela, O., Lederkremer, R.M., (1996) J. Org. Chem., 61, pp. 1886-1889
  • Schenkman, S., Ferguson, M.A., Heise, N., De Almeida, M.L., Mortara, R.A., Yoshida, N., (1993) Mol. Biochem. Parasitol., 59, pp. 293-303
  • Gallo-Rodriguez, C., Varela, O., Lederkremer, R.M., (1998) Carbohydr. Res., 305, pp. 163-170
  • Acosta-Serrano, A., Almeida, I.C., Freitas-Junior, L.H., Yoshida, N., Schenkman, S., (2001) Mol. Biochem. Parasitol., 114, pp. 143-150
  • Haines, A.H., (1976) Adv. Carbohydr. Chem. Biochem., 33, pp. 11-110
  • Bock, K., Pedersen, C., (1983) Adv. Carbohydr. Chem. Biochem., 41, pp. 27-66
  • Gallo-Rodriguez, C., Gandolfi, L., Lederkremer, R.M., (1999) Org. Lett., 1, pp. 245-248
  • Gandolfi-Donadio, L., Gallo-Rodriguez, C., Lederkremer, R.M., (2002) J. Org. Chem., 67, pp. 4430-4435
  • Schmidt, R.R., Stumpp, M., (1983) Liebigs Ann. Chem., pp. 1249-1256
  • Amwam-Zollo, P.H., Sinaÿ, P., (1986) Carbohydr. Res., 150, pp. 199-212
  • Beynon, L.M., Richards, J.C., Perry, M.B., (1997) Eur. J. Biochem., 250, pp. 163-167
  • Zhang, J., Kováǎ, P., (1999) J. Carbohydr. Chem., 18, pp. 461-469
  • Kuhn, R., Baer, H.H., (1958) Ann, 611, pp. 236-241
  • Lerner, L.M., (1972) Methods Carbohydr. Chem., 6, pp. 131-134

Citas:

---------- APA ----------
Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M. & de Lederkremer, R.M. (2002) . Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi. Tetrahedron, 58(46), 9373-9380.
http://dx.doi.org/10.1016/S0040-4020(02)01226-7
---------- CHICAGO ----------
Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., de Lederkremer, R.M. "Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi" . Tetrahedron 58, no. 46 (2002) : 9373-9380.
http://dx.doi.org/10.1016/S0040-4020(02)01226-7
---------- MLA ----------
Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., de Lederkremer, R.M. "Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi" . Tetrahedron, vol. 58, no. 46, 2002, pp. 9373-9380.
http://dx.doi.org/10.1016/S0040-4020(02)01226-7
---------- VANCOUVER ----------
Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., de Lederkremer, R.M. Synthesis of β-D-Galp-(1→3)-β-D-Galp-(1→6)-[β-D-Galf- (1→4)]-D-GlcNAc, a tetrasaccharide component of mucins of Trypanosoma cruzi. Tetrahedron. 2002;58(46):9373-9380.
http://dx.doi.org/10.1016/S0040-4020(02)01226-7