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

Murthy, Bandaru Narasimha ; Sinha, Sharmistha ; Surolia, Avadhesha ; Jayaramana, Narayanaswamy ; Szilàgyi, Làszlò ; Szabò, Ildikò ; Kövér, Katalin E. (2009) Interactions of aromatic mannosyl disulfide derivatives with Concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies Carbohydrate Research, 344 (13). pp. 1758-1763. ISSN 0008-6215

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.carres.2009.06.008

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:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Glycomimetics; Glycosyl Disulfides; Isothermal Titration Calorimetry; Ligand-lectin Interactions; Saturation Transfer Difference (STD) NMR
ID Code:56658
Deposited On:25 Aug 2011 10:27
Last Modified:25 Aug 2011 10:27

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