dc.creator | Gil de Montes Rojas, Enrique | es |
dc.creator | Jiménez Moreno, Ester | es |
dc.creator | Oliveira, Bruno L. | es |
dc.creator | Navo, Claudio D. | es |
dc.creator | Robina Ramírez, Inmaculada | es |
dc.creator | Moreno Vargas, Antonio José | es |
dc.date.accessioned | 2019-07-09T11:21:58Z | |
dc.date.available | 2019-07-09T11:21:58Z | |
dc.date.issued | 2019 | |
dc.identifier.citation | Gil de Montes Rojas, E., Jiménez Moreno, E., Oliveira, B.L., Navo, .D., Robina Ramírez, I. y Moreno Vargas, A.J. (2019). Azabicyclic vinyl sulfones for residue-specific dual protein labelling. Chemical Science, 10 (6), 4515-4522. | |
dc.identifier.issn | 2041-6539 | es |
dc.identifier.uri | https://hdl.handle.net/11441/87965 | |
dc.description.abstract | We have developed [2.2.1]azabicyclic vinyl sulfone reagents that simultaneously enable cysteine-selective protein modification and introduce a handle for further bioorthogonal ligation. The reaction is fast and selective for cysteine relative to other amino acids that have nucleophilic side-chains, and the formed products are stable in human plasma and are moderately resistant to retro Diels–Alder degradation reactions. A model biotinylated [2.2.1]azabicyclic vinyl sulfone reagent was shown to efficiently label two cysteine-tagged proteins, ubiquitin and C2Am, under mild conditions (1–5 equiv. of reagent in NaPi pH 7.0, room temperature, 30 min). The resulting thioether-linked conjugates were stable and retained the native activity of the proteins. Finally, the dienophile present in the azabicyclic moiety on a functionalised C2Am protein could be fluorescently labelled through an inverse electron demand Diels–Alder reaction in cells to allow selective apoptosis imaging. The combined advantages of directness, site-specificity and easy preparation mean [2.2.1]azabicyclic vinyl sulfones can be used for residue-specific dual protein labelling/construction strategies with minimal perturbation of native function based simply on the attachment of an [2.2.1]azabicyclic moiety to cysteine. | es |
dc.description.sponsorship | España Universidad de Sevilla PP2017- 8144 | es |
dc.description.sponsorship | España, Ministerio de Economía y Competitividad Spanish Ministry of Economy and Competitiveness CTQ2016-77270-R , CTQ2015-70524-R, RYC-2013-14706 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | Royal Society of Chemistry | es |
dc.relation.ispartof | Chemical Science, 10 (6), 4515-4522. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.title | Azabicyclic vinyl sulfones for residue-specific dual protein labelling | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/publishedVersion | 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 | CTQ2015-70524-R | es |
dc.relation.projectID | PP2017- 8144 | es |
dc.relation.projectID | RYC-2013-14706 | es |
dc.relation.publisherversion | http://dx.doi.org/10.1039/c9sc00125e | es |
dc.identifier.doi | 10.1039/c9sc00125e | es |
idus.format.extent | 7 p. | es |
dc.journaltitle | Chemical Science | es |
dc.publication.volumen | 10 | es |
dc.publication.issue | 6 | es |
dc.publication.initialPage | 4515 | es |
dc.publication.endPage | 4522 | es |