Investigation of binding affinity of a broad array of L-fucosides with six fucose-specific lectins from bacterial and fungal origin

Le Thai, Son and Mező, Erika and Kelemen, Viktor and Borbás, Anikó (2019) Investigation of binding affinity of a broad array of L-fucosides with six fucose-specific lectins from bacterial and fungal origin. MOLECULES, 24 (12). pp. 2262-2279. ISSN 1420-3049

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Abstract

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 up using copper-mediated azide-alkyne click chemistry. Series of fucoside monomers and dimers were synthesized using various methods, namely glycosylation, azide-alkyne click reaction, photoinduced thiol-en addition and sulfation. The interactions of compounds with six fucolectins of bacterial or fungal origin were tested using hemagglutination inhibition assay. As a result, a tetravalent, α-L-fucose presenting glycocluster showed to be orders of magnitude better ligand than a simple monosaccharide for tested lectins in most cases, which can nominate it as a universal ligand for studied lectins. This compound was also able to inhibit adhesion of Pseudomonas aeruginosa cells to human epithelial bronchial cells. A trivalent fucocluster with protected amine functional group seems also to be a promising candidate to design glycoconjugates and chimeras.

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