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Interactions of aromatic mannosyl disulfide derivatives with Concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies

Murthy, Bandaru Narasimha and Sinha, Sharmistha and Surolia, Avadhesha and Jayaraman, Narayanaswamy and Szilagyi, Laszlo and Szabo, Ildiko and Kover, Katalin E (2009) Interactions of aromatic mannosyl disulfide derivatives with Concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies. In: Carbohydrate Research, 344 (13). pp. 1758-1763.

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Abstract

α-d-Mannopyranosyl units were attached to an aromatic scaffold through disulfide linkages to obtain mono- to trivalent glycosylated ligands for lectin binding studies. Isothermal titration calorimetric (ITC) measurements indicated that binding affinities of these derivatives to Concanavalin A (Con A) were comparable to or slightly higher than that of methyl α-d-mannopyranoside (Ka values in the range of 104 M−1). The stoichiometries of the lectin-ligand complexes were in agreement with the formal valencies (1–3) of the respective ligands indicating cross-linking in interactions with the di- and trivalent derivatives. Multivalency effects could not, however, be observed with the latter. These ligands were shown to bind to the carbohydrate binding site of Con A using saturation transfer difference (STD) NMR competition experiments.

Item Type: Journal Article
Additional Information: Copy right of this article belongs to Elsevier Science.
Keywords: Glycomimetics;Glycosyl disulfides;Isothermal titration calorimetry;Ligand-lectin interactions;Saturation transfer difference (STD) NMR
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 06 Jan 2010 09:07
Last Modified: 19 Sep 2010 05:47
URI: http://eprints.iisc.ernet.in/id/eprint/23836

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