A Minimal, Unstrained S‐Allyl Handle for Pre‐Targeting Diels–Alder Bioorthogonal Labeling in Live Cells. (20th October 2016)

• Record Type: Journal Article
• Authors: Oliveira, Bruno L.; Guo, Zijian; Boutureira, Omar; Guerreiro, Ana; Jiménez‐Osés, Gonzalo; Bernardes, Gonçalo J. L.
• Is Part Of: Angewandte Chemie. Volume 128:Number 47(2016)
• Page Start: 14903
• Page End: 14907
• Publication Date: 2016-10-20
• Subjects: Apoptose -- Bioorthogonale Markierung -- Diels-Alder-Reaktionen -- Pretargeting -- Ungespannte Alkene; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201608438
• Languages: English
• ISSNs: 0044-8249

Abstract

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.