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

Oliveira, B.L. ; Guo, Z. ; Boutureira, O. ; Guerreiro, A. ; Jiménez-Osés, G. ; Bernardes, G.J.L.

Resumen: 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.

Idioma: Inglés

DOI: 10.1002/anie.201608438

Año: 2016

Publicado en: Angewandte Chemie (International ed.) 55, 47 (2016), 14683-14687
ISSN: 1433-7851

Factor impacto JCR: 11.994 (2016)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 13 / 166 = 0.078 (2016) - Q1 - T1

Factor impacto SCIMAGO: 5.953 - Chemistry (miscellaneous) (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/ES/MICINN/RYC-2013-14706
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2015-70524-R

Tipo y forma: Article (Published version)