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

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.

SUBMITTER: Gulumkar V

PROVIDER: S-EPMC8757328 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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

Gulumkar Vijay V Tähtinen Ville V Ali Aliaa A Rahkila Jani J Valle-Delgado Juan José JJ Äärelä Antti A Österberg Monika M Yliperttula Marjo M Virta Pasi P

ACS omega 20211231 1

Bingel cyclopropanation between Buckminster fullerene and a heteroarmed malonate was utilized to produce a hexakis-functionalized C<sub>60</sub> core, with azide and tetrazine units. This orthogonally bifunctional C<sub>60</sub> 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 contro ...[more]

PMID: 35036794

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