Water-soluble polyglycerol dendrimers with two orthogonally reactive core functional groups for one-pot functionalization

The synthesis of a water-soluble polyglycerol dendrimer with two orthogonal functional groups at the core is reported. The two groups, an azide and amine group, are highly reactive toward alkyne and activated ester moieties, respectively. The orthogonality of the two chemical reactions is demonstrated by the ability to conjugate quantitatively either group, independent of the other and in either order. The orthogonal functionalization of the azide- and amine-cored dendrimer can be accomplished in a stepwise or a one-pot synthetic protocol. All resulting bifunctional dendrimers are fully soluble in water as the water-soluble dendritic scaffold decorated with 48 hydroxyl groups on the surface successfully solubilizes both the hydrophobic fluorophore and targeting group.