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Abstract:

Trypanosoma cruzi, the agent of Chagas' disease, expresses on its surface a trans-sialidase (TcTS) that transfers sialic acid from host glycoconjugates to terminal β-galactopyranosyl units of parasite mucins. This process is involved in infection and pathogenesis. The trisaccharide 2,3-di-O-(β-d- galactopyranosyl)-d-galactose 1 is an external unit in the larger oligosaccharides of the mucins and a site for sialylation. The trisaccharide was previously synthesized in our laboratory. The last step of the synthesis was the hydrogenolysis of the crystalline benzyl trisaccharide. Herein we prove that the trisaccharide 1, its alditol 3 and the benzyl glycoside 2 are good acceptors of sialic acid and effective inhibitors of the sialylation of N-acetyllactosamine catalyzed by TcTS. Furthermore, selective sialylation of the 1→3 linked galactopyranose in glycoside 2 was determined by one and two-dimensional NMR analysis. In contrast, the flexible 2,3-di-O-(β-d- galactopyranosyl)-d-galactitol 3 is sialylated in either one of the two possible sites. © 2004 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase
Autor:Agusti, R.; Mendoza, V.M.; Gallo-Rodriguez, C.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Depto. de Quím. Orgán., Fac. Cie. Exact. Y Nat., Univ. B., 1428 Buenos Aires, Argentina
Palabras clave:2,3 di o (beta dextro galactopyranosyl) dextro galactose; alditol; amine; galactose; glycoside; protozoal protein; sialic acid; sialidase; trisaccharide; unclassified drug; article; carbon nuclear magnetic resonance; catalysis; chemical structure; nuclear Overhauser effect; priority journal; proton nuclear magnetic resonance; sialylation; Trypanosoma cruzi
Año:2005
Volumen:16
Número:2
Página de inicio:541
Página de fin:551
DOI: http://dx.doi.org/10.1016/j.tetasy.2004.11.075
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4; sialidase, 9001-67-6
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v16_n2_p541_Agusti

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Citas:

---------- APA ----------
Agusti, R., Mendoza, V.M., Gallo-Rodriguez, C. & De Lederkremer, R.M. (2005) . Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase. Tetrahedron Asymmetry, 16(2), 541-551.
http://dx.doi.org/10.1016/j.tetasy.2004.11.075
---------- CHICAGO ----------
Agusti, R., Mendoza, V.M., Gallo-Rodriguez, C., De Lederkremer, R.M. "Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase" . Tetrahedron Asymmetry 16, no. 2 (2005) : 541-551.
http://dx.doi.org/10.1016/j.tetasy.2004.11.075
---------- MLA ----------
Agusti, R., Mendoza, V.M., Gallo-Rodriguez, C., De Lederkremer, R.M. "Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase" . Tetrahedron Asymmetry, vol. 16, no. 2, 2005, pp. 541-551.
http://dx.doi.org/10.1016/j.tetasy.2004.11.075
---------- VANCOUVER ----------
Agusti, R., Mendoza, V.M., Gallo-Rodriguez, C., De Lederkremer, R.M. Selective sialylation of 2,3-di-O-(β-D-galactopyranosyl)-D-galactose catalyzed by Trypanosoma cruzi trans-sialidase. Tetrahedron Asymmetry. 2005;16(2):541-551.
http://dx.doi.org/10.1016/j.tetasy.2004.11.075