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

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dc.contributor.authorOliveira, Bruno L.
dc.contributor.authorGuo, Zijian
dc.contributor.authorBoutureira, Omar
dc.contributor.authorGuerreiro, Ana
dc.contributor.authorJiménez‐Osés, Gonzalo
dc.contributor.authorBernardes, Gonçalo J. L.
dc.date.accessioned2022-01-18T15:10:32Z
dc.date.available2022-01-18T15:10:32Z
dc.date.issued2016
dc.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.pt_PT
dc.description.abstractThe 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.pt_PT
dc.description.sponsorshipWe 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAngew Chem Int Ed Engl. 2016 Nov 14;55(47):14683-14687pt_PT
dc.identifier.doi10.1002/anie.201608438pt_PT
dc.identifier.eissn1521-3773
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/10451/50878
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWileypt_PT
dc.relationCTQ2015-70524-Rpt_PT
dc.relationRYC-2013-14706pt_PT
dc.relation.publisherversionhttps://onlinelibrary.wiley.com/journal/15213773pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectDiels-Alder reactionspt_PT
dc.subjectApoptosispt_PT
dc.subjectBioorthogonal labelingpt_PT
dc.subjectPre-targetingpt_PT
dc.subjectUnstrained alkenespt_PT
dc.titleA minimal, unstrained S‐Allyl handle for pre‐targeting Diels–Alder bioorthogonal labeling in live cellspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage14687pt_PT
oaire.citation.issue47pt_PT
oaire.citation.startPage14683pt_PT
oaire.citation.titleAngewandte Chemie International Editionpt_PT
oaire.citation.volume55pt_PT
person.familyNamedos Santos Guerreiro
person.familyNameBernardes
person.givenNameAna Maria
person.givenNameGonçalo
person.identifier.ciencia-id481C-A494-B69D
person.identifier.orcid0000-0002-2173-6514
person.identifier.orcid0000-0001-6594-8917
person.identifier.scopus-author-id14046757500
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication1c4166db-cf53-48ab-9e3f-476f142cb304
relation.isAuthorOfPublicationd1a48067-77b1-4413-b1c7-602fb18c62c0
relation.isAuthorOfPublication.latestForDiscoveryd1a48067-77b1-4413-b1c7-602fb18c62c0

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