Selectively Functionalized Glycerol/Diacid Dendrimers via Click Chemistry of Azido Fatty Acids

Dendrimers consisting of glycerol and dicarboxylic acid units were synthesized using a convergent or “outside-in” strategy. The multimeric arms, or dendrons, are joined to a central core in the final step using the azide/alkyne click reaction. The combination of these approaches allows the preparation of dendrimers with variable and controlled degrees of substitution at their periphery. For example, a single protected amino acid has been situated at the periphery, with all other substituents being hydrophobic. In another example, all the peripheral substituents are protected amino acids. The identity of the dendrimers is unambiguous due to the purification and characterization of all the synthetic intermediates. Functional groups have also been selectively incorporated along the arms (dicarboxylic acids) and at the cores.