A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels–Alder Bioorthogonal Labeling in Live Cells

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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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APA

Oliveira, B. L., Guo, Z., Boutureira, O., Guerreiro, A., Jiménez-Osés, G., & Bernardes, G. J. L. (2016). A Minimal, Unstrained S-Allyl Handle for Pre-Targeting Diels–Alder Bioorthogonal Labeling in Live Cells. Angewandte Chemie - International Edition, 55(47), 14683–14687. https://doi.org/10.1002/anie.201608438

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