dc.creator | Gil de Montes, Enrique | es |
dc.creator | Istrate, Alena | es |
dc.creator | Navo, Claudio D. | es |
dc.creator | Jiménez Moreno, Ester | es |
dc.creator | Hoyt, Emily A. | es |
dc.creator | Corzana, Francisco | es |
dc.creator | Robina Ramírez, Inmaculada | es |
dc.creator | Jiménez Osés, Gonzalo | es |
dc.creator | Moreno Vargas, Antonio José | es |
dc.creator | Bernardes, Gonçalo J.L. | es |
dc.date.accessioned | 2022-11-30T15:13:44Z | |
dc.date.available | 2022-11-30T15:13:44Z | |
dc.date.issued | 2020 | |
dc.identifier.citation | Gil de Montes, E., Istrate, A., Navo, C.D., Jiménez Moreno, E., Hoyt, E.A., Corzana, F.,...,Bernardes, G.J.L. (2020). Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation. Angewandte Chemie - International Edition, 59 (15), 6196-6200. https://doi.org/10.1002/anie.201914529. | |
dc.identifier.issn | 1433-7851 | es |
dc.identifier.issn | 1521-3773 | es |
dc.identifier.uri | https://hdl.handle.net/11441/139945 | |
dc.description.abstract | 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. | es |
dc.description.sponsorship | Ministerio de Economía y Competitividad CTQ2016-77270-R, RTI2018-099592-B-C22, RYC-2013-14706, RTI2018-099592-B-C21 | es |
dc.description.sponsorship | Union Europea 701473 | es |
dc.description.sponsorship | Fundación para la Ciencia y la Tecnología IF/00624/2015 | es |
dc.description.sponsorship | Consejo Europeo de Investigación 676832 | es |
dc.format | application/pdf | es |
dc.format.extent | 6 p. | es |
dc.language.iso | eng | es |
dc.publisher | Wiley-Blackwell | es |
dc.relation.ispartof | Angewandte Chemie - International Edition, 59 (15), 6196-6200. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Bioconjugation | es |
dc.subject | Chemical biology | es |
dc.subject | Cycloaddition | es |
dc.subject | Heterocycles | es |
dc.subject | Proteins | es |
dc.title | Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/acceptedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | CTQ2016-77270-R | es |
dc.relation.projectID | RTI2018-099592-B-C22 | es |
dc.relation.projectID | RYC-2013-14706 | es |
dc.relation.projectID | RTI2018-099592-B-C21 | es |
dc.relation.projectID | IF/00624/2015 | es |
dc.relation.projectID | 676832 | es |
dc.relation.publisherversion | https://dx.doi.org/10.1002/anie.201914529 | es |
dc.identifier.doi | 10.1002/anie.201914529 | es |
dc.journaltitle | Angewandte Chemie - International Edition | es |
dc.publication.volumen | 59 | es |
dc.publication.issue | 15 | es |
dc.publication.initialPage | 6196 | es |
dc.publication.endPage | 6200 | es |
dc.contributor.funder | Ministerio de Economía y Competitividad (MINECO). España | es |
dc.contributor.funder | Union Europea | es |
dc.contributor.funder | Fundación para la Ciencia y la Tecnología. Portugal | es |
dc.contributor.funder | Consejo Europeo de Investigación | es |