Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups

In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro-1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol...

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Autores: Sharma, Anamika, Kumar, Ashish, El-Faham, Ayman, de la Torre, Beatriz G., Albericio, Fernando
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/239140
Acceso en línea:http://hdl.handle.net/10261/239140
Access Level:acceso abierto
Palabra clave:Linker
Orthogonality
Orthogonal chemoselectivity
Solid-phase peptide synthesis
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spelling Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groupsSharma, AnamikaKumar, AshishEl-Faham, Aymande la Torre, Beatriz G.Albericio, FernandoLinkerOrthogonalityOrthogonal chemoselectivitySolid-phase peptide synthesisIn the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro-1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 °C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 °C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the α and ε amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.The work was funded in part by the National Research Foundation (NRF) (# 105892 and Blue Sky’s Research Programme # 120386) The authors extend their appreciation to the Researchers Supporting Project at King Saud University, Riyadh, Saudi Arabia for funding this work through Project No. RSP-2020/50.Peer reviewedElsevierConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202120212020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/239140reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.1016/j.bioorg.2020.104334Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2391402026-05-22T06:33:51Z
dc.title.none.fl_str_mv Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
title Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
spellingShingle Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
Sharma, Anamika
Linker
Orthogonality
Orthogonal chemoselectivity
Solid-phase peptide synthesis
title_short Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
title_full Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
title_fullStr Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
title_full_unstemmed Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
title_sort Exploiting azido-dichloro-triazine as a linker for regioselective incorporation of peptides through their N, O, S functional groups
dc.creator.none.fl_str_mv Sharma, Anamika
Kumar, Ashish
El-Faham, Ayman
de la Torre, Beatriz G.
Albericio, Fernando
author Sharma, Anamika
author_facet Sharma, Anamika
Kumar, Ashish
El-Faham, Ayman
de la Torre, Beatriz G.
Albericio, Fernando
author_role author
author2 Kumar, Ashish
El-Faham, Ayman
de la Torre, Beatriz G.
Albericio, Fernando
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Linker
Orthogonality
Orthogonal chemoselectivity
Solid-phase peptide synthesis
topic Linker
Orthogonality
Orthogonal chemoselectivity
Solid-phase peptide synthesis
description In the field of bioconjugation, linker development has witnessed massive growth in recent years. 2,4,6-Trichloro-1,3,5-triazine (TCT) is a tridentate linker that can accommodate three distinct nucleophiles. Herein, the reaction of azido triazine derivatives with nucleophiles (amine, thiol and phenol) is studied. The replacement of first chlorine was performed at 0 °C while that of the last chlorine was achieved successfully at rt. As a proof of concept of this strategy with potential application in biological studies, pentapeptides (Ac-XGGFL-NH2 where X = Lys or Tyr or Cys) were reacted with 2-azido-4,6-dichlorotriazine to replace the first and second chlorine at 0 °C and at rt, respectively. The reactivity of 2-azido-4,6-dichlorotriazine was found to be similar for the α and ε amine group present in same peptide. These findings demonstrate the applicability of 2-azido-4,6-dichlorotriazine as a linker with potential further application in bioconjugation.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/239140
url http://hdl.handle.net/10261/239140
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.1016/j.bioorg.2020.104334
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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