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Abstract:

The mucin-like glycoproteins of Trypanosoma cruzi have novel O-linked oligosaccharides that are acceptors of sialic acid in the trans-sialidase (TcTS) reaction. The transference of sialic acid from host glycoconjugates to the mucins is involved in infection and pathogenesis. The synthesis of the pentasaccharide, β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-β-d-Galp-(1→6)-[β-d-Galf-(1→4)]-d-GlcpNAc and the corresponding alditol, previously isolated by reductive β-elimination of the mucins, is described. The key step was the 6-O-glycosylation of a easily accessible derivative of β-d-Galf-(1→4)-d-GlcpNAc with a β-d-Galp-(1→2)-[β-d-Galp-(1→3)]-d-Galp donor using the trichloroacetimidate method. The β-linkage was diastereoselectively obtained by the nitrile effect. The pentasaccharide is the major oligosaccharide in the mucins of T. cruzi, G strain and presents two terminal β-d-Galp residues for possible sialylation by TcTS. A preparative sialylation reaction was performed with its benzyl glycoside and the sialylated product was isolated and characterized. NMR spectroscopic analysis showed that selective monosialylation occurred at the terminal (1→3) linked galactopyranose. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase
Autor:Mendoza, V.M.; Agusti, R.; Gallo-Rodriguez, C.; de Lederkremer, R.M.
Filiación:CIHIDECAR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Palabras clave:Galactofuranose; Pentasaccharide; Sialic acid; trans-Sialidase; Trichloroacetimidate glycosylation; Trypanosoma cruzi; Nuclear magnetic resonance; Organic acids; Proteins; Reaction kinetics; Reduction; Synthesis (chemical); Galactofuranose; Pentasaccharides; Sialic acid; trans-Sialidase; Trichloroacetimidate glycosylation; Trypanosoma cruzi; Saccharification; alditol; glycoconjugate; glycoprotein; mucin; nitrile; oligosaccharide; pentasaccharide; sialic acid; sialidase; trichloroacetimidic acid; article; carbohydrate synthesis; elimination reaction; glycosylation; isolation procedure; nonhuman; nuclear magnetic resonance spectroscopy; priority journal; sialylation; stereochemistry; Trypanosoma cruzi; Animals; Carbohydrate Sequence; Glycoproteins; Molecular Sequence Data; Mucins; Neuraminidase; Nuclear Magnetic Resonance, Biomolecular; Oligosaccharides; Recombinant Proteins; Trypanosoma cruzi; Trypanosoma cruzi
Año:2006
Volumen:341
Número:10
Página de inicio:1488
Página de fin:1497
DOI: http://dx.doi.org/10.1016/j.carres.2006.03.033
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:sialidase, 9001-67-6; Glycoproteins; Mucins; Neuraminidase, EC 3.2.1.18; Oligosaccharides; Recombinant Proteins; trans-sialidase, EC 3.2.1.-
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n10_p1488_Mendoza

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Citas:

---------- APA ----------
Mendoza, V.M., Agusti, R., Gallo-Rodriguez, C. & de Lederkremer, R.M. (2006) . Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase. Carbohydrate Research, 341(10), 1488-1497.
http://dx.doi.org/10.1016/j.carres.2006.03.033
---------- CHICAGO ----------
Mendoza, V.M., Agusti, R., Gallo-Rodriguez, C., de Lederkremer, R.M. "Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase" . Carbohydrate Research 341, no. 10 (2006) : 1488-1497.
http://dx.doi.org/10.1016/j.carres.2006.03.033
---------- MLA ----------
Mendoza, V.M., Agusti, R., Gallo-Rodriguez, C., de Lederkremer, R.M. "Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase" . Carbohydrate Research, vol. 341, no. 10, 2006, pp. 1488-1497.
http://dx.doi.org/10.1016/j.carres.2006.03.033
---------- VANCOUVER ----------
Mendoza, V.M., Agusti, R., Gallo-Rodriguez, C., de Lederkremer, R.M. Synthesis of the O-linked pentasaccharide in glycoproteins of Trypanosoma cruzi and selective sialylation by recombinant trans-sialidase. Carbohydr. Res. 2006;341(10):1488-1497.
http://dx.doi.org/10.1016/j.carres.2006.03.033