Synthesis of an Azide- and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules

Bingel cyclopropanation between Buckminster fullerene and a heteroarmed malonate was utilized to produce a hexakis-functionalized C-60 core, with azide and tetrazine units. This orthogonally bifunctional C-60 scaffold can be selectively one-pot functionalized by two pericyclic click reactions, that is, inverse electron-demand Diels-Alder and azide-alkyne cycloaddition, which with appropriate ligands (monosaccharides, a peptide and oligonucleotides tested) allows one to control the assembly of heteroantennary bioconjugates.

Automated summary

The Bingel cyclopropanation reaction was used to produce a hexakis-functionalized C-60 core, which can be selectively functionalized by two pericyclic click reactions, allowing control over the assembly of heteroantennary bioconjugates with appropriate ligands.