title: A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels-Alder Bioorthogonal Labeling in Live Cells.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK.
authors.forename: Bruno L
authors.initials: BL
authors.lastname: Oliveira
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK.
authors.forename: Zijian
authors.initials: Z
authors.lastname: Guo
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK.
authors.forename: Omar
authors.identifier: 0000-0002-0768-8309
authors.initials: O
authors.lastname: Boutureira
authors.affiliation: Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028, Lisboa, Portugal.
authors.forename: Ana
authors.initials: A
authors.lastname: Guerreiro
authors.affiliation: Departamento de Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química, 26006, Logroño, Spain.|Institute of Biocomputation and Physics of Complex Systems (BIFI), University of Zaragoza, BIFI-IQFR (CSIC), Zaragoza, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK.|Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028, Lisboa, Portugal.
authors.forename: Gonçalo J L
authors.identifier: 0000-0001-6594-8917
authors.initials: GJ
authors.lastname: Bernardes
mesh_terms: D061565:Cycloaddition Reaction; D057809:HEK293 Cells; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013777:Tetrazoles
keywords: Diels-Alder reactions; apoptosis; bioorthogonal labeling; pre-targeting; unstrained alkenes