1. Synthesis of an Azide-and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules
- Author
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Vijay Gulumkar, Ville Tähtinen, Aliaa Ali, Jani Rahkila, Juan José Valle-Delgado, Antti Äärelä, Monika Österberg, Marjo Yliperttula, Pasi Virta, University of Turku, Åbo Akademi University, Department of Bioproducts and Biosystems, University of Helsinki, Aalto-yliopisto, Aalto University, Division of Pharmaceutical Biosciences, Biopharmaceutics Group, and Drug Research Program
- Subjects
CATALYZED ALKYNE-AZIDE ,010405 organic chemistry ,General Chemical Engineering ,MALEIMIDE ,General Chemistry ,HEXAKIS-ADDUCTS ,010402 general chemistry ,01 natural sciences ,SCAFFOLDS ,Article ,0104 chemical sciences ,Chemistry ,317 Pharmacy ,CLICK CHEMISTRY ,CYCLOOCTYNE ,C-60 ,FULLERENE ,QD1-999 - Abstract
Funding Information: V.G. and P.V. acknowledge Academy of Finland’s Project No. 308931. J.J.V.D. and M.Ö. acknowledge Academy of Finland’s Flagship Programme under Project Nos. 318890 and 318891 (Competence Center for Materials Bioeconomy, FinnCERES). M.Y. acknowledges Academy of Finland’s Flagship Programme under Project No. 337430 (Gene, Cell and Nano Therapy Competence Cluster for the Treatment of Chronic Diseases, GeneCellNano). Publisher Copyright: © 2021 The Authors. Published by American Chemical Society. 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.
- Published
- 2022