“Onion peel” glycodendrimer syntheses using mixed triazine and cyclotriphosphazene scaffolds

Abstract

An expeditious synthetic protocol for the construction of glycodendrimers is illustrated using the newly discovered “onion peel” strategy. The onion peel approach and orthogonal coupling strategies were accomplished with rationally design sequential modifications of cyanuric acid. Carefully chosen building blocks and their effective attachment by chemoselective atom economical click reactions, namely Cu (I) azide–alkyne cycloaddition reaction (CuAAC) and photocatalyzed thiol-ene reaction (TEC), allowed rapid build-up of glycodendrimers in contrast to traditional dendrimers syntheses that are based on the repetitive use of identical building blocks to form each layer. The newly formed glycodendrimers were evaluated for their capacity to cross-link carbohydrate-lectin interactions using dynamic light scattering (DLS). Rapid increase in particle size was observed as a function of time when compared to their monomer counterparts resulting from the multivalent lectin cross-linking ability of the new glycodendrimers.