Polysialosides scaffolded on p-Tert-butylcalix[4]arene

Solution and Crystal Structures of a Sugar Binding Site Mutant of Cyanovirin-N: No Evidence of Domain Swapping

“…Therefore, each protein may bind more than one carbohydrate epitope simultaneously (Lee, 1992; Bundle et al, 1992). Results using model systems revealed that (i) polyvalent display of carbohydrates produces high avidities, although the affinities of monovalent, small sugars for their protein receptors are weak (Kiessling and Pohl, 1996; Sigal et al, 1996; Adler et al, 1995; Sabesan et al, 1991; DeFrees et al, 1996; Spengard et al, 1996; Meunier and Roy, 1996) and (ii) increased specificity may results from carbohydrates being presented in a polyvalent format (Lees et al, 1994; Mortell et al, 1996). Approaches aimed at understanding the molecular mechanisms and structural basis of high-affinity oligosaccharide recognition, as well as the energetic principles that govern these important interactions, ideally combine structural information derived from NMR or crystallography with thermodynamic data provided by isothermal titration calorimetry.…”

Recognition of exterior protein surfaces using artificial ligands based on calixarenes, crown ethers, and tetraphenylporphyrins

“…Submillimolar concentrations of tetra-and octavalent sialoside clusters inhibited hemagglutination and viral infectivity mediated by BK and influenza A viruses. Roy and co-workers prepared calixarene derivatives with sialic acid and N-acetyl-galactosamine units on their lower rims [55,56]. Dendritic, water-soluble, carbohydrate-containing p-tert-butylcalix [4]arene was synthesized to study the lectin-binding properties.…”

Amphiphilicp-tert-Butylcalix[4]arene Scaffolds Containing Exposed Carbohydrate Dendrons

“…[2] In spite of these interesting featuresÐand in addition possible variation of conformational organization, substitution of the upper and lower rims, and shape and sizeÐonly limited efforts have been made to construct biologically relevant calixarenes containing carbohydrate moieties. [3, 4] In line with this concept, the synthesis of nondendritic galactose octamers attached to a calix[4]resorcarene scaffold possessing lipophilic side chains has been described. However, as opposed to our work presented herein, the hydrophilic carbohydrate residues were used for polar attachment to a polar quartz surface.…”