Dependence of Concanavalin A Binding on Anomeric Configuration, Linkage Type, and Ligand Multiplicity for Thiourea-Bridged Mannopyranosyl–β-Cyclodextrin Conjugates

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

“…97 mannosyl display to the mannose-binding sites in the lectin. 101 To overcome this limitation, the incorporation of different spacer segments between the CD core and the polyamino groups as well as between the glycoligands and the isothiocyanate functionality has been proposed. Santoyo-González, Roy and co-workers implemented the use of p-isothiocyanatophenyl glycosides in reaction with the amino-terminated per-(C-6)-thioalkyl derivative 31, 85,86 whereas Ortiz Mellet, Defaye, García Fernández and coworkers coupled aliphatic isothiocyanate-armed thioglycosides and the per-(C-6)-cysteaminyl bCD derivative 32 as a heptanucleophile.…”

Carbohydrate Microarrays

“…A direct application of the method would be the rapid diagnosis of infectious diseases. [16] In any case, probing of microspotted slides containing appropriately tethered N-acetyl-D-glucosamine, lactose, maltose, and cellobiose ligands with FITC-tagged lectins showed a binding pattern identical to that in solution ( Figure 2); this demonstrates that microarrays prepared by this technique allow thousands of carbohydrate ± protein binding assays (up to 12 000 microspots in this work) to be performed in a parallel fashion. More robust immobilization techniques may be necessary for those channels, especially when low-molecularweight recognition epitopes are involved.…”

Synthesis of cyclodextrin derivatives with monosaccharides and their binding with ampicillin and selected lectins

“…1 Cyclodextrins (CDs) offer unique features towards the formation of glycoclusters for biological applications, since they are biocompatible and can be easily modified in their primary side with carbohydrate moieties. Per-carbohydrate modified CD derivatives have been reported [6][7][8][9][10][11][12][13][14][15] demonstrating the advantages of multivalency and clustering effect in homo-and heterogeneously decorated cyclodextrin scaffolds. Herein, the synthesis of a series of new cyclodextrin-based glycoclusters with seven and eight monosaccharide units connected to the CD core via optimally sized linkers, as well as the corresponding monosubstituted derivatives, is reported.…”