A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells

Detalhes bibliográficos
Autor(a) principal: Oliveira, Bruno L.
Data de Publicação: 2016
Outros Autores: Guo, Zijian, Boutureira, Omar, Guerreiro, Ana, Jiménez‐Osés, Gonzalo, Bernardes, Gonçalo J. L.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10451/50878
Resumo: © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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spelling A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cellsDiels-Alder reactionsApoptosisBioorthogonal labelingPre-targetingUnstrained alkenes© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.The unstrained S-allyl cysteine amino acid was site-specifically installed on apoptosis protein biomarkers and was further used as a chemical handle and ligation partner for 1,2,4,5-tetrazines by means of an inverse-electron-demand Diels-Alder reaction. We demonstrate the utility of this minimal handle for the efficient labeling of apoptotic cells using a fluorogenic tetrazine dye in a pre-targeting approach. The small size, easy chemical installation, and selective reactivity of the S-allyl handle towards tetrazines should be readily extendable to other proteins and biomolecules, which could facilitate their labeling within live cells.We thank China Scholarship Council (PhD studentship to Z.G.), FCT Portugal (FCT Investigator to G.J.L.B.), and the EU (Marie-Sklodowska Curie ITN Protein Conjugates; Marie-Sklodowska Curie IEF to B.L.O. and O.B.), MINECO (CTQ2015-70524-R and RYC-2013-14706 to G.J.O.), and the EPSRC for funding.WileyRepositório da Universidade de LisboaOliveira, Bruno L.Guo, ZijianBoutureira, OmarGuerreiro, AnaJiménez‐Osés, GonzaloBernardes, Gonçalo J. L.2022-01-18T15:10:32Z20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10451/50878engAngew Chem Int Ed Engl. 2016 Nov 14;55(47):14683-146871433-785110.1002/anie.2016084381521-3773info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-08T16:55:15Zoai:repositorio.ul.pt:10451/50878Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T22:02:14.345277Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
title A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
spellingShingle A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
Oliveira, Bruno L.
Diels-Alder reactions
Apoptosis
Bioorthogonal labeling
Pre-targeting
Unstrained alkenes
title_short A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
title_full A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
title_fullStr A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
title_full_unstemmed A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
title_sort A minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cells
author Oliveira, Bruno L.
author_facet Oliveira, Bruno L.
Guo, Zijian
Boutureira, Omar
Guerreiro, Ana
Jiménez‐Osés, Gonzalo
Bernardes, Gonçalo J. L.
author_role author
author2 Guo, Zijian
Boutureira, Omar
Guerreiro, Ana
Jiménez‐Osés, Gonzalo
Bernardes, Gonçalo J. L.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Repositório da Universidade de Lisboa
dc.contributor.author.fl_str_mv Oliveira, Bruno L.
Guo, Zijian
Boutureira, Omar
Guerreiro, Ana
Jiménez‐Osés, Gonzalo
Bernardes, Gonçalo J. L.
dc.subject.por.fl_str_mv Diels-Alder reactions
Apoptosis
Bioorthogonal labeling
Pre-targeting
Unstrained alkenes
topic Diels-Alder reactions
Apoptosis
Bioorthogonal labeling
Pre-targeting
Unstrained alkenes
description © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016-01-01T00:00:00Z
2022-01-18T15:10:32Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10451/50878
url http://hdl.handle.net/10451/50878
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14683-14687
1433-7851
10.1002/anie.201608438
1521-3773
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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