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Abstract:

We report here the synthesis of divalent ligands containing 3-deoxy-4-thiolactose. This thiodisaccharide has been synthesized using the Michael addition of β-1-thiogalactose to the α,β-unsaturated system of sugar-derived dihydropyranones, followed by the reduction of the remaining carbonyl group. We were able to control the configuration (S) of the stereocenter linked to sulfur (C-4) of the reducing end by conducting the thioglycosylation at high temperature or by isomerization during the reduction of the 2-ulose thiodisaccharide with NaBH4/THF. The energy profile for this reaction on a model compound was calculated. The anomeric position of the 3-deoxy-4-thiolactose was functionalized with a terminal alkyne, which was coupled to azide-containing sugar scaffolds through CuAAC reaction to afford mono- and divalent ligands. The final products were competitive inhibitors of E. coli β-galactosidase in the micromolar range. Their binding affinities to peanut agglutinin (PNA) were determined by isothermal calorimetry, which showed a clear decrease in the Ka values for monovalent derivatives compared to lactose. This report contributes to establishing the role of a particular hydroxyl group of lactose in sugar-protein recognition processes. © The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose
Autor:Cagnoni, A.J.; Varela, O.; Kovensky, J.; Uhrig, M.L.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 1428 Buenos Aires, Argentina
LABORATOIRE des GLUCIDES-CNRS, Université de Picardie Jules Verne, FRE 3517, 10 rue Baudelocque, 80039 Amiens Cedex, France
Palabras clave:Addition reactions; Binding energy; Bioactivity; Chelation; Escherichia coli; Sugars; Synthesis (chemical); Anomeric position; Binding affinities; High temperature; Isothermal calorimetry; Michael additions; Micromolar range; Peanut agglutinins (PNA); Recognition process; Ligands; Arachis hypogaea
Año:2013
Volumen:11
Número:33
Página de inicio:5500
Página de fin:5511
DOI: http://dx.doi.org/10.1039/c3ob41074a
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v11_n33_p5500_Cagnoni

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Citas:

---------- APA ----------
Cagnoni, A.J., Varela, O., Kovensky, J. & Uhrig, M.L. (2013) . Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose. Organic and Biomolecular Chemistry, 11(33), 5500-5511.
http://dx.doi.org/10.1039/c3ob41074a
---------- CHICAGO ----------
Cagnoni, A.J., Varela, O., Kovensky, J., Uhrig, M.L. "Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose" . Organic and Biomolecular Chemistry 11, no. 33 (2013) : 5500-5511.
http://dx.doi.org/10.1039/c3ob41074a
---------- MLA ----------
Cagnoni, A.J., Varela, O., Kovensky, J., Uhrig, M.L. "Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose" . Organic and Biomolecular Chemistry, vol. 11, no. 33, 2013, pp. 5500-5511.
http://dx.doi.org/10.1039/c3ob41074a
---------- VANCOUVER ----------
Cagnoni, A.J., Varela, O., Kovensky, J., Uhrig, M.L. Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose. Org. Biomol. Chem. 2013;11(33):5500-5511.
http://dx.doi.org/10.1039/c3ob41074a