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

[Image: see text] 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 cl...

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Detalles Bibliográficos
Autores principales: Gulumkar, Vijay, Tähtinen, Ville, Ali, Aliaa, Rahkila, Jani, Valle-Delgado, Juan José, Äärelä, Antti, Österberg, Monika, Yliperttula, Marjo, Virta, Pasi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8757328/
https://www.ncbi.nlm.nih.gov/pubmed/35036794
http://dx.doi.org/10.1021/acsomega.1c05955
Descripción
Sumario:[Image: see text] 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.

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