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dc.contributor.authorGil de Montes, Enriqueen
dc.contributor.authorIstrate, Alenaen
dc.contributor.authorNavo, Claudio Den
dc.contributor.authorJiménez-Moreno, Esteren
dc.contributor.authorHoyt, Emily Aen
dc.contributor.authorCorzana, Franciscoen
dc.contributor.authorRobina, Inmaculadaen
dc.contributor.authorJiménez-Osés, Gonzaloen
dc.contributor.authorMoreno-Vargas, Antonio Jen
dc.contributor.authorLopes Bernardes, Goncaloen
dc.date.accessioned2020-02-01T00:30:30Z
dc.date.available2020-02-01T00:30:30Z
dc.date.issued2020-04en
dc.identifier.issn1433-7851
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/301534
dc.description.abstractWe have developed an azanorbornadiene bromovinyl sulfone reagent that allows cysteine-selective bioconjugation. Subsequent reaction with dipyridyl tetrazine led 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 lends it to the routine preparation of protein conjugates for chemical biology studies.
dc.format.mediumPrint-Electronicen
dc.languageengen
dc.publisherWiley
dc.rightsAll rights reserved
dc.subjectAza Compoundsen
dc.subjectNorbornanesen
dc.subjectCysteineen
dc.subjectPyrrolesen
dc.subjectCycloaddition Reactionen
dc.titleStable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation.en
dc.typeArticle
prism.endingPage6200
prism.issueIdentifier15en
prism.publicationDate2020en
prism.publicationNameAngewandte Chemie (International ed. in English)en
prism.startingPage6196
prism.volume59en
dc.identifier.doi10.17863/CAM.48603
dcterms.dateAccepted2020-01-23en
rioxxterms.versionofrecord10.1002/anie.201914529en
rioxxterms.versionAM
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserveden
rioxxterms.licenseref.startdate2020-04en
dc.contributor.orcidGil de Montes, Enrique [0000-0003-2635-7086]
dc.contributor.orcidNavo, Claudio D [0000-0003-0161-412X]
dc.contributor.orcidCorzana, Francisco [0000-0001-5597-8127]
dc.contributor.orcidRobina, Inmaculada [0000-0003-1447-8032]
dc.contributor.orcidMoreno-Vargas, Antonio J [0000-0002-5771-2012]
dc.contributor.orcidBernardes, Goncalo [0000-0001-6594-8917]
dc.identifier.eissn1521-3773
rioxxterms.typeJournal Article/Reviewen
pubs.funder-project-idEuropean Commission Horizon 2020 (H2020) ERC (676832)
pubs.funder-project-idRoyal Society (URF\R\180019)
pubs.funder-project-idEuropean Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (701473)
cam.orpheus.successTue Mar 31 10:36:51 BST 2020 - Embargo updated*
rioxxterms.freetoread.startdate2021-01-25


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