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Chemodivergent manganese-catalyzed C–H activation: modular synthesis of fluorogenic probes

Author

Listed:
  • Nikolaos Kaplaneris

    (Georg-August-Universität Göttingen)

  • Jongwoo Son

    (Georg-August-Universität Göttingen)

  • Lorena Mendive-Tapia

    (The University of Edinburgh)

  • Adelina Kopp

    (Georg-August-Universität Göttingen)

  • Nicole D. Barth

    (The University of Edinburgh)

  • Isaac Maksso

    (Georg-August-Universität Göttingen)

  • Marc Vendrell

    (The University of Edinburgh)

  • Lutz Ackermann

    (Georg-August-Universität Göttingen
    German Centre for Cardiovascular Research (DZHK))

Abstract

Bioorthogonal late-stage diversification of amino acids and peptides bears enormous potential for drug discovery and molecular imaging. Despite major accomplishments, these strategies largely rely on traditional, lengthy prefunctionalization methods, heavily involving precious transition-metal catalysis. Herein, we report on a resource-economical manganese(I)-catalyzed C–H fluorescent labeling of structurally complex peptides ensured by direct alkynylation and alkenylation manifolds. This modular strategy sets the stage for unraveling structure-activity relationships between structurally discrete fluorophores towards the rational design of BODIPY fluorogenic probes for real-time analysis of immune cell function.

Suggested Citation

  • Nikolaos Kaplaneris & Jongwoo Son & Lorena Mendive-Tapia & Adelina Kopp & Nicole D. Barth & Isaac Maksso & Marc Vendrell & Lutz Ackermann, 2021. "Chemodivergent manganese-catalyzed C–H activation: modular synthesis of fluorogenic probes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23462-9
    DOI: 10.1038/s41467-021-23462-9
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