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

  1. Oliveira, B.L. 2
  2. Guo, Z. 2
  3. Boutureira, O. 2
  4. Guerreiro, A. 4
  5. Jiménez-Osés, G. 13
  6. Bernardes, G.J.L. 24
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 University of Cambridge
    info

    University of Cambridge

    Cambridge, Reino Unido

    ROR https://ror.org/013meh722

  3. 3 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

  4. 4 Universidade de Lisboa
    info

    Universidade de Lisboa

    Lisboa, Portugal

    ROR https://ror.org/01c27hj86

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Revista:
Angewandte Chemie International

ISSN: 1433-7851

Año de publicación: 2016

Volumen: 55

Número: 47

Páginas: 14683-14687

Tipo: Artículo

DOI: 10.1002/ANIE.201608438 SCOPUS: 2-s2.0-84995581663 WoS: WOS:000388252700033 GOOGLE SCHOLAR

Otras publicaciones en: Angewandte Chemie International

Repositorio institucional: lock_openAcceso abierto Editor

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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. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim