Synthesis of a model trisaccharide for studying the interplay between the anti α-Gal antibody and the trans-sialidase reactions in Trypanosoma cruzi
Trypanosoma cruzi, the etiologic agent of Chagas disease, is covered by a dense glycocalix mainly composed by glycoproteins called mucins which are also the acceptors of sialic acid in a reaction catalyzed by a trans-sialidase (TcTS). Sialylation of trypomastigote mucins protects the parasite from l...
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Elsevier Ltd
2017
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| 005 | 20230518204848.0 | ||
| 008 | 190410s2017 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-85028308862 | |
| 024 | 7 | |2 cas |a sialidase, 9001-67-6; Antibodies; Calcium-Binding Proteins; galactose-binding protein; Glycoproteins; Monosaccharide Transport Proteins; Neuraminidase; Periplasmic Binding Proteins; trans-sialidase; Trisaccharides | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Giorgi, M.E. | |
| 245 | 1 | 0 | |a Synthesis of a model trisaccharide for studying the interplay between the anti α-Gal antibody and the trans-sialidase reactions in Trypanosoma cruzi |
| 260 | |b Elsevier Ltd |c 2017 | ||
| 270 | 1 | 0 | |m Marino, C.; CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Argentina; email: cmarino@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 520 | 3 | |a Trypanosoma cruzi, the etiologic agent of Chagas disease, is covered by a dense glycocalix mainly composed by glycoproteins called mucins which are also the acceptors of sialic acid in a reaction catalyzed by a trans-sialidase (TcTS). Sialylation of trypomastigote mucins protects the parasite from lysis by the anti α-Galp antibodies from serum. The TcTS is essential for the infection process since T. cruzi is unable to biosynthesize sialic acid. The enzyme specifically transfers it from a terminal β-D-Galp unit in the host glycoconjugate to terminal β-D-Galp units in the parasite mucins to construct the D-NeuNAc(α2→3)β-D-Galp motif. On the other hand, although galactose is the most abundant sugar in mucins of both, the infective trypomastigotes and the insect stage epimastigotes, α-D-Galp is only present in the infective stage whereas β-D-Galf is characteristic of the epimastigote stage of the less virulent strains. Neither α-D-Galp nor D-Galf is acceptor of sialic acid. In the mucins, some of the oligosaccharides are branched with terminal β-D-Galp units to be able to accept sialic acid in the TcTS reaction. Based on previous reports showing that anti α-Galp antibodies only partially colocalize with sialic acid, we have undertaken the synthesis of the trisaccharide α-D-Galp(1→3)-[β-D-Galp(1→6)]-D-Galp, the smallest structure containing both, the antigenic D-Galp(α1→3)-D-Galp unit and the sialic acid-acceptor β-D-Galp unit. The trisaccharide was obtained as the 6-aminohexyl glycoside to facilitate further conjugation for biochemical studies. The synthetic approach involved the α-galactosylation at O-4 of a suitable precursor of the reducing end, followed by β-galactosylation at O-6 of the same precursor and introduction of the 6-aminohexyl aglycone. The fully deprotected trisaccharide was successfully sialylated by TcTS using either 3′-sialyllactose or fetuin as donors. The product, 6-aminohexyl α-D-NeuNAc(2→3)-β-D-Galp(1→6)-[α-D-Galp(1→3)]-β-D-Galp, was purified and characterized. © 2017 Elsevier Ltd |l eng | |
| 536 | |a Detalles de la financiación: Universidad Nacional de San Luis | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción CientÃfica y Tecnológica, PICT 2014 0471 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, PIP 2015-2017 11220150100366CO | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones CientÃficas y Técnicas | ||
| 536 | |a Detalles de la financiación: Yaddo, 2014-2017 20020130100114BA | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones CientÃficas y Técnicas | ||
| 536 | |a Detalles de la financiación: We thank O. Campetella and his group from Universidad Nacional General San Martín, Argentina, for the kind gift of recombinant trans-sialidase of T.cruzi . This work was supported by grants from Universidad de Buenos Aires ( PIP 2015-2017 11220150100366CO ), Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT) ( PICT 2014 0471 ) and Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) (UBACyT 2014-2017 20020130100004BA y UBACyT 2014-2017 20020130100114BA) of Argentina. M.E.G., R.A., C.M. and R.M.L. are Research Members of CONICET. R.L. was supported by a fellowship from ANPCyT . Appendix A | ||
| 593 | |a Universidad de Buenos Aires, Consejo Nacional de Investigaciones Científicas y Técnicas, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTI Α-GAL |
| 690 | 1 | 0 | |a TRANS-SIALIDASE |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a CARBOXYLIC ACIDS |
| 690 | 1 | 0 | |a BIOCHEMICAL STUDIES |
| 690 | 1 | 0 | |a ETIOLOGIC AGENTS |
| 690 | 1 | 0 | |a INFECTION PROCESS |
| 690 | 1 | 0 | |a REACTION CATALYZED |
| 690 | 1 | 0 | |a SYNTHETIC APPROACH |
| 690 | 1 | 0 | |a TRANS-SIALIDASES |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a VIRULENT STRAINS |
| 690 | 1 | 0 | |a ANTIBODIES |
| 690 | 1 | 0 | |a 6 AMINOHEXYL GLYCOSIDE |
| 690 | 1 | 0 | |a GLYCOSIDE |
| 690 | 1 | 0 | |a SIALIDASE |
| 690 | 1 | 0 | |a TRISACCHARIDE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANTIBODY |
| 690 | 1 | 0 | |a CALCIUM BINDING PROTEIN |
| 690 | 1 | 0 | |a GALACTOSE-BINDING PROTEIN |
| 690 | 1 | 0 | |a GLUCOSE TRANSPORTER |
| 690 | 1 | 0 | |a GLYCOPROTEIN |
| 690 | 1 | 0 | |a PERIPLASMIC BINDING PROTEIN |
| 690 | 1 | 0 | |a SIALIDASE |
| 690 | 1 | 0 | |a TRANS-SIALIDASE |
| 690 | 1 | 0 | |a TRISACCHARIDE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BIOCHEMICAL ANALYSIS |
| 690 | 1 | 0 | |a CARBOHYDRATE SYNTHESIS |
| 690 | 1 | 0 | |a CONJUGATION |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a SIALYLATION |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a CARBOHYDRATE ANALYSIS |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a IMMUNOLOGY |
| 690 | 1 | 0 | |a METABOLISM |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 690 | 1 | 0 | |a ANTIBODIES |
| 690 | 1 | 0 | |a CALCIUM-BINDING PROTEINS |
| 690 | 1 | 0 | |a CARBOHYDRATE SEQUENCE |
| 690 | 1 | 0 | |a CHEMISTRY TECHNIQUES, SYNTHETIC |
| 690 | 1 | 0 | |a GLYCOPROTEINS |
| 690 | 1 | 0 | |a MONOSACCHARIDE TRANSPORT PROTEINS |
| 690 | 1 | 0 | |a NEURAMINIDASE |
| 690 | 1 | 0 | |a PERIPLASMIC BINDING PROTEINS |
| 690 | 1 | 0 | |a TRISACCHARIDES |
| 690 | 1 | 0 | |a TRYPANOSOMA CRUZI |
| 700 | 1 | |a Lopez, R. | |
| 700 | 1 | |a Agusti, R. | |
| 700 | 1 | |a Marino, C. | |
| 700 | 1 | |a de Lederkremer, R.M. | |
| 773 | 0 | |d Elsevier Ltd, 2017 |g v. 450 |h pp. 30-37 |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
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