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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 O-linked chains may contain galactofuranose in addition to the acceptor galactopyranose units. Thus far, the galactofuranose form was found in the mucins of strains belonging to the less infective lineage. The acceptor properties of the chemically synthesized oligosaccharides were now studied in order to correlate their structure with the ability to act as substrates. Recombinant TcTS and sialyllactose as donor were used. The reactions were followed by HPAEC-PAD. The Km values were calculated for the free sugars, the sugar alditols and the benzyl glycosides. All the compounds showed to be good acceptors of sialic acid. Thus, the introduction of galactofuranose in the mucins of the strains of lineage 1 would not be responsible for the diminished virulence of the strains. The oligosaccharides and derivatives inhibited the transfer of sialic acid to the substrate N-acetyllactosamine with IC50 values between 0.6 and 4 mM. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose
Autor:Agustí, R.; Giorgi, M.E.; Mendoza, V.M.; 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; HPAEC-PAD; Mucins; trans-Sialidase; Trypanosoma cruzi; alditol; amine; benzyl glycoside; carbohydrate derivative; galactofuranose; galactopyranose; glycoside; lactose; monosaccharide; mucin; n acetyllactosamine; oligosaccharide; recombinant enzyme; sialic acid; sialidase; sialyllactose; sugar; unclassified drug; article; carbohydrate synthesis; comparative study; drug synthesis; enzyme mechanism; enzyme substrate; IC 50; nonhuman; parasite virulence; protozoal infection; sialylation; strain identification; structure activity relation; transport kinetics; Trypanosoma cruzi; Amino Sugars; Animals; Carbohydrate Sequence; Escherichia coli; Galactose; Kinetics; Molecular Sequence Data; Mucins; Neuraminidase; Oligosaccharides; Recombinant Proteins; Sialic Acids; Trypanosoma cruzi; Trypanosoma cruzi
Año:2007
Volumen:15
Número:7
Página de inicio:2611
Página de fin:2616
DOI: http://dx.doi.org/10.1016/j.bmc.2007.01.045
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:galactopyranose, 40825-89-6; lactose, 10039-26-6, 16984-38-6, 63-42-3, 64044-51-5; sialidase, 9001-67-6; Amino Sugars; Galactose, 26566-61-0; Mucins; N-acetyllactosamine, 32181-59-2; Neuraminidase, 3.2.1.18; Oligosaccharides; Recombinant Proteins; Sialic Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v15_n7_p2611_Agusti

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Citas:

---------- APA ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Gallo-Rodriguez, C. & de Lederkremer, R.M. (2007) . Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose. Bioorganic and Medicinal Chemistry, 15(7), 2611-2616.
http://dx.doi.org/10.1016/j.bmc.2007.01.045
---------- CHICAGO ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Gallo-Rodriguez, C., de Lederkremer, R.M. "Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose" . Bioorganic and Medicinal Chemistry 15, no. 7 (2007) : 2611-2616.
http://dx.doi.org/10.1016/j.bmc.2007.01.045
---------- MLA ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Gallo-Rodriguez, C., de Lederkremer, R.M. "Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose" . Bioorganic and Medicinal Chemistry, vol. 15, no. 7, 2007, pp. 2611-2616.
http://dx.doi.org/10.1016/j.bmc.2007.01.045
---------- VANCOUVER ----------
Agustí, R., Giorgi, M.E., Mendoza, V.M., Gallo-Rodriguez, C., de Lederkremer, R.M. Comparative rates of sialylation by recombinant trans-sialidase and inhibitor properties of synthetic oligosaccharides from Trypanosoma cruzi mucins-containing galactofuranose and galactopyranose. Bioorg. Med. Chem. 2007;15(7):2611-2616.
http://dx.doi.org/10.1016/j.bmc.2007.01.045