Investigation of the Binding Affinity of a Broad Array of l-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin

Investigation of the Binding Affinity of a Broad Array of l-Fucosides with Six Fucose-Specific Lectins of Bacterial and Fungal Origin

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Series of multivalent α-l-fucoside containing glycoclusters and variously decorated l-fucosides were synthesized to find potential inhibitors of fucose-specific lectins and study the structure-binding affinity relationships.Tri- and tetravalent fucoclusters were built using copper-mediated azide-alkyne click chemistry.Series of fucoside monomers and dimers were synthesized using various methods, namely glycosylation, an azide-alkyne click reaction, photoinduced thiol-en addition, and sulfation.The interactions bostik universal primer pro between compounds with six fucolectins of bacterial or fungal origin were tested using a hemagglutination inhibition assay.

As a result, a tetravalent, α-l-fucose presenting glycocluster showed to be a ligand that was orders of magnitude better than a simple monosaccharide for tested abc material lectins in most cases, which can nominate it as a universal ligand for studied lectins.This compound was also able to inhibit the adhesion of Pseudomonas aeruginosa cells to human epithelial bronchial cells.A trivalent fucocluster with a protected amine functional group also seems to be a promising candidate for designing glycoconjugates and chimeras.