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Abstract:

The first synthesis of methyl β-d-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of l-altrofuranose (16) or d-galactofuranose (18) as the reducing end, are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf found in glycoconjugates of many pathogenic microorganisms. The conformational preferences of 16 and 18 in solution were assessed by means of molecular modeling and NMR techniques. These thiodisaccharides have been evaluated as inhibitors of the β-d-galactofuranosidase from Penicillium fellutanum. The kinetics of the inhibition showed that they behave as competitive inhibitors. As expected, compound 18 (Ki = 0.15 mM), with the same configuration for the reducing end as the natural substrate of the enzyme, was a stronger inhibitor than 16 (Ki = 2.23 mM). This journal is © The Royal Society of Chemistry 2015.

Registro:

Documento: Artículo
Título:Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase
Autor:Lo Fiego, M.J.; Marino, C.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina
INQUISUR-CONICET, Departamento de Química, Universidad Nacional Del sur, Avenida Alem 1253, Bahía Blanca, 8000, Argentina
Palabras clave:Conformational preferences; Galactofuranose; Glycoconjugates; Glycomimetics; Natural substrates; NMR techniques; Pathogenic microorganisms; Reducing ends; Microorganisms
Año:2015
Volumen:5
Número:57
Página de inicio:45631
Página de fin:45640
DOI: http://dx.doi.org/10.1039/c5ra06899a
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n57_p45631_LoFiego

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Citas:

---------- APA ----------
Lo Fiego, M.J., Marino, C. & Varela, O. (2015) . Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase. RSC Advances, 5(57), 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a
---------- CHICAGO ----------
Lo Fiego, M.J., Marino, C., Varela, O. "Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase" . RSC Advances 5, no. 57 (2015) : 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a
---------- MLA ----------
Lo Fiego, M.J., Marino, C., Varela, O. "Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase" . RSC Advances, vol. 5, no. 57, 2015, pp. 45631-45640.
http://dx.doi.org/10.1039/c5ra06899a
---------- VANCOUVER ----------
Lo Fiego, M.J., Marino, C., Varela, O. Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase. RSC Adv. 2015;5(57):45631-45640.
http://dx.doi.org/10.1039/c5ra06899a