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^*

^*Tämän työn vastaava kirjoittaja

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

1 Sitaatiot (Scopus)

17 Lataukset (Pure)

Abstrakti

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.

Alkuperäiskieli	Englanti
Sivut	1329–1336
Sivumäärä	8
Julkaisu	ACS Omega
Vuosikerta	7
Numero	1
Varhainen verkossa julkaisun päivämäärä	31 jouluk. 2021
DOI - pysyväislinkit	https://doi.org/10.1021/acsomega.1c05955
Tila	Julkaistu - 11 tammik. 2022
OKM-julkaisutyyppi	A1 Julkaistu artikkeli, soviteltu

Pääsy asiakirjaan

10.1021/acsomega.1c05955Lisenssi: CC BY

CHEM_Gulumkar_et_al_Synthesis_of_an_Azide_and_Tetrazine_Functionalized_2022_ACS_OmegaFinal published version, 3,95 MBLisenssi: CC BY

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1 Aktiivinen

CERES: Competence Center for the materials Bioeconomy: A Flagship for our Sustainable Future
Mäkelä, K.
01/05/2018 → 31/12/2022
Projekti: Academy of Finland: Other research funding

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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",

month = jan,

day = "11",

doi = "10.1021/acsomega.1c05955",

language = "English",

volume = "7",

pages = "1329–1336",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "AMERICAN CHEMICAL SOCIETY",

number = "1",

}

Synthesis of an Azide-and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules. / Gulumkar, Vijay; Tähtinen, Ville; Ali, Aliaa; Rahkila, Jani; Valle-Delgado, Juan José; Äärelä, Antti; Österberg, Monika; Yliperttula, Marjo; Virta, Pasi.

julkaisussa: ACS Omega, Vuosikerta 7, Nro 1, 11.01.2022, s. 1329–1336.

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

TY - JOUR

T1 - Synthesis of an Azide-and Tetrazine-Functionalized [60]Fullerene and Its Controlled Decoration with Biomolecules

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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U2 - 10.1021/acsomega.1c05955

DO - 10.1021/acsomega.1c05955

M3 - Article

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VL - 7

SP - 1329

EP - 1336

JO - ACS Omega

JF - ACS Omega

SN - 2470-1343

IS - 1

ER -

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

Abstrakti

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SFX-saatavuus

Muut tiedostot ja linkit

Sormenjälki

Projektit

CERES: Competence Center for the materials Bioeconomy: A Flagship for our Sustainable Future

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