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

Vijay Gulumkar; Ville Tähtinen; Aliaa Ali; Jani Rahkila; Juan José Valle-Delgado; Antti Äärelä; Monika Österberg; Marjo Yliperttula; Pasi Virta

doi:10.1021/acsomega.1c05955

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

ACS Omega. 2021 Dec 31;7(1):1329-1336. doi: 10.1021/acsomega.1c05955. eCollection 2022 Jan 11.

Authors

Vijay Gulumkar¹, Ville Tähtinen¹, Aliaa Ali¹, Jani Rahkila², Juan José Valle-Delgado³, Antti Äärelä¹, Monika Österberg³, Marjo Yliperttula⁴, Pasi Virta¹

Affiliations

¹ Department of Chemistry, University of Turku, FI-20500 Turku, Finland.
² Instrument Centre, Faculty of Science and Engineering, Åbo Akademi University, FI-20500 Åbo, Finland.
³ Department of Bioproducts and Biosystems, Aalto University, FI-00076 Aalto, Finland.
⁴ Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki, FI-00014 Helsinki, Finland.

Abstract

Bingel cyclopropanation between Buckminster fullerene and a heteroarmed malonate was utilized to produce a hexakis-functionalized C₆₀ core, with azide and tetrazine units. This orthogonally bifunctional C₆₀ 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.