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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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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.

Original language	English
Pages (from-to)	1329–1336
Number of pages	8
Journal	ACS Omega
Volume	7
Issue number	1
Early online date	31 Dec 2021
DOIs	https://doi.org/10.1021/acsomega.1c05955
Publication status	Published - 11 Jan 2022
MoE publication type	A1 Journal article-refereed

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CHEM_Gulumkar_et_al_Synthesis_of_an_Azide_and_Tetrazine_Functionalized_2022_ACS_OmegaFinal published version, 3.95 MBLicence: CC BY

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@article{16820d56d11a4b999e3b6f3ec1176207,

title = "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. ",

author = "Vijay Gulumkar and Ville T{\"a}htinen and Aliaa Ali and Jani Rahkila and Valle-Delgado, {Juan Jos{\'e}} and Antti {\"A}{\"a}rel{\"a} and Monika {\"O}sterberg and Marjo Yliperttula and Pasi Virta",

note = "Funding Information: V.G. and P.V. acknowledge Academy of Finland{\textquoteright}s Project No. 308931. J.J.V.D. and M.{\"O}. acknowledge Academy of Finland{\textquoteright}s Flagship Programme under Project Nos. 318890 and 318891 (Competence Center for Materials Bioeconomy, FinnCERES). M.Y. acknowledges Academy of Finland{\textquoteright}s Flagship Programme under Project No. 337430 (Gene, Cell and Nano Therapy Competence Cluster for the Treatment of Chronic Diseases, GeneCellNano). Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society.",

year = "2022",

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journal = "ACS Omega",

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AU - Gulumkar, Vijay

AU - Tähtinen, Ville

AU - Ali, Aliaa

AU - Rahkila, Jani

AU - Valle-Delgado, Juan José

AU - Äärelä, Antti

AU - Österberg, Monika

AU - Yliperttula, Marjo

AU - Virta, Pasi

N1 - 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.

PY - 2022/1/11

Y1 - 2022/1/11

N2 - 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.

AB - 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.

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

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FinnCERES: Competence Center for the Materials Bioeconomy: A Flagship for our Sustainable Future

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

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FinnCERES: Competence Center for the Materials Bioeconomy: A Flagship for our Sustainable Future

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