Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation

An azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged prote...

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Detalles Bibliográficos
Autores: Gil de Montes, Enrique, Istrate, Alena, Navo, Claudio D., Jiménez Moreno, Ester, Hoyt, Emily A., Corzana, Francisco, Robina Ramírez, Inmaculada, Jiménez Osés, Gonzalo, Moreno Vargas, Antonio José, Bernardes, Gonçalo J.L.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/139945
Acceso en línea:https://hdl.handle.net/11441/139945
https://doi.org/10.1002/anie.201914529
Access Level:acceso abierto
Palabra clave:Bioconjugation
Chemical biology
Cycloaddition
Heterocycles
Proteins
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spelling Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene FragmentationGil de Montes, EnriqueIstrate, AlenaNavo, Claudio D.Jiménez Moreno, EsterHoyt, Emily A.Corzana, FranciscoRobina Ramírez, InmaculadaJiménez Osés, GonzaloMoreno Vargas, Antonio JoséBernardes, Gonçalo J.L.BioconjugationChemical biologyCycloadditionHeterocyclesProteinsAn azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged protein through inverse electron demand Diels–Alder cycloaddition with subsequent double retro-Diels–Alder reactions to form a stable pyrrole linkage. The sequence of site-selective bioconjugation followed by bioorthogonal bond cleavage was efficiently employed for the labelling of three different proteins. This method benefits from easy preparation of these reagents, selectivity for cysteine, and stability after reaction with a commercial tetrazine, which has potential for the routine preparation of protein conjugates for chemical biology studies.Ministerio de Economía y Competitividad CTQ2016-77270-R, RTI2018-099592-B-C22, RYC-2013-14706, RTI2018-099592-B-C21Union Europea 701473Fundación para la Ciencia y la Tecnología IF/00624/2015Consejo Europeo de Investigación 676832Wiley-BlackwellQuímica OrgánicaMinisterio de Economía y Competitividad (MINECO). EspañaUnion EuropeaFundación para la Ciencia y la Tecnología. PortugalConsejo Europeo de Investigación2020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/139945https://doi.org/10.1002/anie.201914529reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésAngewandte Chemie - International Edition, 59 (15), 6196-6200.CTQ2016-77270-RRTI2018-099592-B-C22RYC-2013-14706RTI2018-099592-B-C21IF/00624/2015676832https://dx.doi.org/10.1002/anie.201914529info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1399452026-06-17T12:51:07Z
dc.title.none.fl_str_mv Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
title Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
spellingShingle Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
Gil de Montes, Enrique
Bioconjugation
Chemical biology
Cycloaddition
Heterocycles
Proteins
title_short Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
title_full Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
title_fullStr Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
title_full_unstemmed Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
title_sort Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
dc.creator.none.fl_str_mv Gil de Montes, Enrique
Istrate, Alena
Navo, Claudio D.
Jiménez Moreno, Ester
Hoyt, Emily A.
Corzana, Francisco
Robina Ramírez, Inmaculada
Jiménez Osés, Gonzalo
Moreno Vargas, Antonio José
Bernardes, Gonçalo J.L.
author Gil de Montes, Enrique
author_facet Gil de Montes, Enrique
Istrate, Alena
Navo, Claudio D.
Jiménez Moreno, Ester
Hoyt, Emily A.
Corzana, Francisco
Robina Ramírez, Inmaculada
Jiménez Osés, Gonzalo
Moreno Vargas, Antonio José
Bernardes, Gonçalo J.L.
author_role author
author2 Istrate, Alena
Navo, Claudio D.
Jiménez Moreno, Ester
Hoyt, Emily A.
Corzana, Francisco
Robina Ramírez, Inmaculada
Jiménez Osés, Gonzalo
Moreno Vargas, Antonio José
Bernardes, Gonçalo J.L.
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
Ministerio de Economía y Competitividad (MINECO). España
Union Europea
Fundación para la Ciencia y la Tecnología. Portugal
Consejo Europeo de Investigación
dc.subject.none.fl_str_mv Bioconjugation
Chemical biology
Cycloaddition
Heterocycles
Proteins
topic Bioconjugation
Chemical biology
Cycloaddition
Heterocycles
Proteins
description An azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged protein through inverse electron demand Diels–Alder cycloaddition with subsequent double retro-Diels–Alder reactions to form a stable pyrrole linkage. The sequence of site-selective bioconjugation followed by bioorthogonal bond cleavage was efficiently employed for the labelling of three different proteins. This method benefits from easy preparation of these reagents, selectivity for cysteine, and stability after reaction with a commercial tetrazine, which has potential for the routine preparation of protein conjugates for chemical biology studies.
publishDate 2020
dc.date.none.fl_str_mv 2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/139945
https://doi.org/10.1002/anie.201914529
url https://hdl.handle.net/11441/139945
https://doi.org/10.1002/anie.201914529
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Angewandte Chemie - International Edition, 59 (15), 6196-6200.
CTQ2016-77270-R
RTI2018-099592-B-C22
RYC-2013-14706
RTI2018-099592-B-C21
IF/00624/2015
676832
https://dx.doi.org/10.1002/anie.201914529
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley-Blackwell
publisher.none.fl_str_mv Wiley-Blackwell
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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