A Minimal,Unstrained S‐Allyl Handle for Pre‐Targeting Diels–Alder Bioorthogonal Labeling in Live Cells |
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| Authors: | Dr Bruno L Oliveira Zijian Guo Dr Omar Boutureira Ana Guerreiro Dr Gonzalo Jiménez‐Osés Dr Gonçalo J L Bernardes |
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| Affiliation: | 1. Department of Chemistry, University of Cambridge, Cambridge, UK;2. Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Lisboa, Portugal;3. Departamento de Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química, Logro?o, Spain;4. Institute of Biocomputation and Physics of Complex Systems (BIFI), University of Zaragoza, Zaragoza, Spain |
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| 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. |
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| Keywords: | apoptosis bioorthogonal labeling Diels– Alder reactions pre-targeting unstrained alkenes |
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