Navegar

Colección

Datos Estadísticas

Artículo

El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The hexasaccharide β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-β-d-Galp-(1→6)-[β-d-Galp(1→2)-β-d-Galf(1→4)]-d-GlcNAc (10) and its β-d-Galf-(1→2)-β-d-Galf containing isomer (7) are the largest carbohydrates in mucins of some strains of Trypanosoma cruzi. The terminal β-d-Galp units are sites of sialylation by the parasite trans-sialidase. Hexasaccharide 10 was chemically synthesized for the first time by a [3+3] nitrilium based convergent approach, using the trichloroacetimidate method of glycosylation. The 1H NMR spectrum of its alditol was identical to the spectrum of the product released by β-elimination from the parasite mucin. The trans-sialylation reaction studied on the benzyl glycoside of 10 showed two monosialylated products whose relative abundance changed with time. On the other hand, only one product was produced by sialylation of the benzyl glycoside of 7. A preparative synthesis of the latter and spectroscopic analysis of the product unequivocally established the sialylation site at the less hindered (1→3)-linked galactopyranose. © 2015 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides
Autor:Agustí, R.; Giorgi, M.E.; Mendoza, V.M.; Kashiwagi, G.A.; De Lederkremer, R.M.; Gallo-Rodriguez, C.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Pabellón II, Buenos Aires, 1428, Argentina
Palabras clave:Galactofuranose; Glycosylation; Mucins trans-Sialidase; Nitrilium; Oligosaccharides; Trypanosoma cruzi; beta dextro galactofuranosyl (1-2) beta dextro galactofuranosyl; beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy alpha,beta dextro glucopyranose; beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] 2 acetamido 2 deoxy dextro glucitol; beta dextro galactopyranosyl (1-2) [beta dextro galactopyranosyl (1-3)] beta dextro galactopyranosyl (1-6) [beta dextro galactopyranosyl (1-2) beta dextro galactofuranosyl (1-4)] dextro n acetylglutamic acid; carbohydrate derivative; glycoside; trichloroacetimidic acid; unclassified drug; glycoprotein; mucin; oligosaccharide; sialidase; trans-sialidase; Article; carbohydrate analysis; carbohydrate synthesis; enzyme kinetics; enzyme structure; glycosylation; nonhuman; proton nuclear magnetic resonance; sialylation; spectroscopy; Trypanosoma cruzi; chemistry; conformation; metabolism; molecular genetics; synthesis; Trypanosoma cruzi; Trypanosoma cruzi; Carbohydrate Conformation; Carbohydrate Sequence; Glycoproteins; Molecular Sequence Data; Mucins; Neuraminidase; Oligosaccharides; Trypanosoma cruzi
Año:2015
Volumen:23
Número:6
Página de inicio:1213
Página de fin:1222
DOI: http://dx.doi.org/10.1016/j.bmc.2015.01.056
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:sialidase, 9001-67-6; Glycoproteins; Mucins; Neuraminidase; Oligosaccharides; trans-sialidase
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v23_n6_p1213_Agusti

Referencias:

  • Brener, Z., (1973) Annu. Rev. Microbiol., 27, p. 347
  • Moncayo, A., (2003) Mem. Inst. Oswaldo Cruz., 98, p. 577
  • Lederkremer, R.M., Agustí, R., (2009) Adv. Carbohydr. Chem. Biochem., 62, p. 31
  • Buscaglia, C.A., Campo, V.A., Frasch, A.C.C., Di Noia, J.M., (2006) Nat. Rev. Microbiol., 4, p. 229
  • Pereira-Chioccola, V.L., Acosta-Serrano, A., Correira De Almeida, I., Ferguson, M.A.J., Souto-Padron, T., Rodrigues, M.M., Travassos, L.R., Schenkman, S., (2000) J. Cell Sci., 113, p. 1299
  • Schenkman, S., Jiang, M.S., Hart, G.W., Nussenzweig, V., (1991) Cell, 65, p. 1117
  • Frasch, A.C.C., (2000) Parasitol. Today, 16, p. 282
  • Ferrero-Garcia, M.A., Trombetta, S.E., Sanchez, D.O., Reglero, A., Frasch, A.C.C., Parodi, A.J., (1993) Eur. J. Biochem., 213, p. 765
  • Harrison, J.A., Kartha, K.P.R., Fournier, E.J.L., Lowary, T.L., Malet, C., Nilsson, U.J., Hindsgaul, O., Field, R.A., (2011) Org. Biomol. Chem., 9, pp. 1653-1660
  • Acosta-Serrano, A., Schenkman, S., Yoshida, N., Mehlert, A., Richardson, J.M., Ferguson, M.A.J., (1995) J. Biol. Chem., 270, p. 27244
  • Previato, J.O., Jones, C., Gonçalves, L.P.B., Wait, R., Travassos, L.R., Mendonça-Previato, L., (1994) Biochem. J., 301, p. 151
  • Agrellos, O.A., Jones, C., Todeschini, A.R., Previato, J.O., Mendonça-Previato, L., (2003) Mol. Biochem. Parasitol., 126, p. 93
  • Todeschini, A.R., De Almeida, E.G., Agrellos, O.A., Jones, C., Previato, J.O., Mendonca-Previato, L., (2009) Mem. Inst. Oswaldo Cruz, 104, p. 270
  • Zingales, B., Andrade, S.G., Briones, M.R., Campbell, D.A., Chiari, E., Fernandes, O., Guhl, F., Schijman, A.G., (2009) Mem. Inst. Oswaldo Cruz., 104, p. 1051
  • Jones, C., Todeschini, A.R., Agrellos, O.A., Previato, J.O., Mendonça-Previato, L., (2004) Biochemistry, 43, p. 11889
  • Agustí, R., Giorgi, M.E., Mendoza, V.M., Gallo-Rodriguez, C., Lederkremer, R.M., (2007) Bioorg. Med. Chem., 15, p. 2611
  • De Arruda, M.V., Colli, W., Zingales, B., (1989) Eur. J. Biochem., 182, p. 413
  • Previato, J.O., Jones, C., Gonçalves, P.B., Wait, R., Travassos, L.R., Parodi, A.J., Mendonça-Previato, L., (1995) J. Biol. Chem., 270, p. 7241
  • Salto, M.L., Gallo-Rodriguez, C., Lima, C., Lederkremer, R.M., (2000) Anal. Biochem., 279, p. 79
  • 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, p. 27671
  • Todeschini, A.R., Da Silveira, E.X., Jones, C., Wait, R., Previato, J.O., Mendonça-Previato, L., (2001) Glycobiology, 11, p. 47
  • Van Well, R.M., Collet, B.Y.M., Field, R.A., (2008) Synlett, p. 2175
  • Gallo-Rodriguez, C., Varela, O., Lederkremer, R.M., (1996) J. Org. Chem., 61, p. 1886
  • Gallo-Rodriguez, C., Varela, O., Lederkremer, R.M., (1998) Carbohydr. Res., 305, p. 163
  • Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., Lederkremer, R.M., (2002) Tetrahedron, 58, p. 9373
  • Mendoza, V.M., Agusti, R., Gallo-Rodriguez, C., Lederkremer, R.M., (2006) Carbohydr. Res., 341, p. 1488
  • Mendoza, V.M., Kashiwagi, G.A., Lederkremer, R.M., Gallo-Rodriguez, C., (2010) Carbohydr. Res., 345, p. 385
  • Kashiwagi, G.A., Mendoza, V.M., Lederkremer, R.M., Gallo-Rodriguez, C., (2012) Org. Biomol. Chem., 10, p. 6322
  • Schmidt, R.R., Jung, K.-H., (1997) Preparative Carbohydrate Chemistry, p. 283. , S. Hanessian, Marcel Dekker
  • Schmidt, R.R., Behrendt, M., Toepfer, A., (1990) Synlett, p. 694
  • Pougny, J.-R., Sinay, P., (1976) Tetrahedron Lett., p. 4073
  • Ratcliffe, A.J., Fraser-Reid, B., (1990) J. Chem. Soc., Perkin Trans. 1, p. 747
  • Bohé, L., Crich, D., (2011) C.R. Chim., 14, p. 3
  • Schmidt, R.R., Zhu, X., Glycosyl Trichloroacetimidates (2008) Glycoscience, p. 451. , B. Fraser-Reid, K. Tatsuta, J. Thiem, Springer Berlin Heidelberg
  • Schmidt, R.R., Kinzy, W., (1994) Adv. Carbohydr. Chem. Biochem., 50, p. 21
  • Agustí, R., Mendoza, V.M., Gallo-Rodriguez, C., Lederkremer, R.M., (2005) Tetrahedron: Asymmetry, 16, p. 541
  • Veh, R.W., Michalski, J., Corfield, A.P., Sander-Wewer, M., Gies, D., Schauer, R., (1981) J. Chromatogr., A, 212, p. 313

Citas:

---------- APA ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M. & Gallo-Rodriguez, C. (2015) . Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides. Bioorganic and Medicinal Chemistry, 23(6), 1213-1222.
http://dx.doi.org/10.1016/j.bmc.2015.01.056
---------- CHICAGO ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides" . Bioorganic and Medicinal Chemistry 23, no. 6 (2015) : 1213-1222.
http://dx.doi.org/10.1016/j.bmc.2015.01.056
---------- MLA ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M., Gallo-Rodriguez, C. "Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides" . Bioorganic and Medicinal Chemistry, vol. 23, no. 6, 2015, pp. 1213-1222.
http://dx.doi.org/10.1016/j.bmc.2015.01.056
---------- VANCOUVER ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Kashiwagi, G.A., De Lederkremer, R.M., Gallo-Rodriguez, C. Synthesis of the O-linked hexasaccharide containing β-d-Galp-(1→2)-d-Galf in Trypanosoma cruzi mucins. Differences on sialylation by trans-sialidase of the two constituent hexasaccharides. Bioorg. Med. Chem. 2015;23(6):1213-1222.
http://dx.doi.org/10.1016/j.bmc.2015.01.056