Synthesis of glycodendrimers containing both fucoside and galactoside residues and their binding properties to Pa-IL and PA-IIL lectins from Pseudomonas aeruginosa

Abstract

Homo- and hetero-bifunctional glycodendrimers ending with up to 16 fucoside and/or galactoside residues were synthesized in good yields using a convergent approach. The biologically active surface carbohydrate moieties were assembled in a single and efficient step using “click chemistry”. The relative binding and cross-linking abilities of these glycodendrimers were evaluated by turbidimetric analyses using both PA-IL and PA-IIL lectins from Pseudomonas aeruginosa. Insoluble complexes were rapidly observed from the first and second generations as well as from the mixed glycodendrimer 32. This hetero-bifunctional glycodendrimer was also evaluated with PA-IL alone and showed potent cross-linking properties. These novel heterobifunctional glycodendrimers may therefore constitute strong antiadhesin properties.