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

Bandaru Narasimha Murthy, Sharmistha Sinha, Avadhesha Surolia, Narayanaswamy Jayaraman, László Szilágyi, Ildikó Szabó, Katalin E. Kövér

Research output: Contribution to journalArticle

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1758-1763
Number of pages6
JournalCarbohydrate Research
Volume344
Issue number13
DOIs
Publication statusPublished - Sep 8 2009

Keywords

  • Glycomimetics
  • Glycosyl disulfides
  • Isothermal titration calorimetry
  • Ligand-lectin interactions
  • Saturation transfer difference (STD) NMR

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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