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Wiley, Angewandte Chemie International Edition, 47(55), p. 14683-14687, 2016

DOI: 10.1002/anie.201608438

Wiley, Angewandte Chemie, 47(128), p. 14903-14907, 2016

DOI: 10.1002/ange.201608438

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

Journal article published in 2016 by Bruno L. Oliveira ORCID, Zijian Guo, Omar Boutureira ORCID, Ana Guerreiro, Gonzalo Jiménez Osés ORCID, Gonçalo J. L. Bernardes ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.