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

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Gulumkar , V , Tähtinen , V , Ali , A , Rahkila , J , Valle-Delgado , J J , Äärelä , A , Österberg , M , Yliperttula , M & Virta , P 2022 , ' Synthesis of an Azide- and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules ' , ACS Omega , vol. 7 , no. 1 , pp. 1329–1336 . https://doi.org/10.1021/acsomega.1c05955

Title: Synthesis of an Azide- and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules
Author: Gulumkar, Vijay; Tähtinen, Ville; Ali, Aliaa; Rahkila, Jani; Valle-Delgado, Juan Jose; Äärelä, Antti; Österberg, Monika; Yliperttula, Marjo; Virta, Pasi
Contributor organization: Division of Pharmaceutical Biosciences
Biopharmaceutics Group
Drug Research Program
Date: 2022-01
Language: eng
Number of pages: 8
Belongs to series: ACS Omega
ISSN: 2470-1343
DOI: https://doi.org/10.1021/acsomega.1c05955
URI: http://hdl.handle.net/10138/340305
Abstract: 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.
Subject: CATALYZED ALKYNE-AZIDE
CLICK CHEMISTRY
HEXAKIS-ADDUCTS
FULLERENE
C-60
CYCLOOCTYNE
SCAFFOLDS
MALEIMIDE
317 Pharmacy
Peer reviewed: Yes
Rights: cc_by
Usage restriction: openAccess
Self-archived version: publishedVersion


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