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Abstract:

In this work we describe the synthesis of mono- and divalent β-N - and β-S-galactopyranosides and related lactosides built on sugar scaffolds and their evaluation as substrates and inhibitors of the Trypanosoma cruzi trans-sialidase (TcTS). This enzyme catalyzes the transfer of sialic acid from an oligosaccharidic donor in the host, to parasite βGalp terminal units and it has been demonstrated that it plays an important role in the infection. Herein, the enzyme was also tested as a tool for the chemoenzymatic synthesis of sialic acid containing glycoclusters. The transfer reaction of sialic acid was performed using a recombinant TcTS and 3'-sialyllactose as sialic acid donor, in the presence of the acceptor having βGalp non reducing ends. The products were analyzed by high performance anion exchange chromatography with pulse amperometric detection (HPAEC-PAD). The ability of the different S-linked and N-linked glycosides to inhibit the sialic acid transfer reaction from 3'-sialyllactose to the natural substrate N-acetyllactosamine, was also studied. Most of the substrates behaved as good acceptors and moderate competitive inhibitors. A di-N -lactoside showed to be the strongest competitive inhibitor among the compounds tested (70% inhibition at equimolar concentration). The usefulness of the enzymatic trans-sialylation for the preparation of sialylated ligands was assessed by performing a preparative sialylation of a divalent substrate, which afforded the monosialylated compound as main product, together with the disialylated glycocluster. © 2014 Cano et al; licensee Beilstein-Institut. License and terms: see end of document.

Registro:

Documento: Artículo
Título:Synthesis of divalent ligands of β-thio- And β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase
Autor:Cano, M.E.; Agusti, R.; Cagnoni, A.J.; Tesoriero, M.F.; Kovensky, J.; Uhrig, M.L.; De Lederkremer, R.M.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Laboratoire de Glycochimie, Des Antimicrobiens et des Agroressources (LG2A)-CNRS FRE 3517, Université de Picardie Jules Verne, 33 rue Saint Leu, Amiens Cedex, 80039, France
Palabras clave:Multivalent ligands; Sialic acid; Sugar scaffolds; T. Cruzi trans-sialidase; β-galactopyranosides
Año:2014
Volumen:10
Página de inicio:3073
Página de fin:3086
DOI: http://dx.doi.org/10.3762/bjoc.10.324
Título revista:Beilstein Journal of Organic Chemistry
Título revista abreviado:Beilstein J. Org. Chem.
ISSN:18605397
CODEN:BJOCB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18605397_v10_n_p3073_Cano

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Citas:

---------- APA ----------
Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L. & De Lederkremer, R.M. (2014) . Synthesis of divalent ligands of β-thio- And β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase. Beilstein Journal of Organic Chemistry, 10, 3073-3086.
http://dx.doi.org/10.3762/bjoc.10.324
---------- CHICAGO ----------
Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L., et al. "Synthesis of divalent ligands of β-thio- And β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase" . Beilstein Journal of Organic Chemistry 10 (2014) : 3073-3086.
http://dx.doi.org/10.3762/bjoc.10.324
---------- MLA ----------
Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L., et al. "Synthesis of divalent ligands of β-thio- And β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase" . Beilstein Journal of Organic Chemistry, vol. 10, 2014, pp. 3073-3086.
http://dx.doi.org/10.3762/bjoc.10.324
---------- VANCOUVER ----------
Cano, M.E., Agusti, R., Cagnoni, A.J., Tesoriero, M.F., Kovensky, J., Uhrig, M.L., et al. Synthesis of divalent ligands of β-thio- And β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase. Beilstein J. Org. Chem. 2014;10:3073-3086.
http://dx.doi.org/10.3762/bjoc.10.324