BODIPY Peptide Labeling by Late-Stage C(sp3 )-H Activation

Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10554-10558. doi: 10.1002/anie.201804654. Epub 2018 Jul 3.

Abstract

Late-stage BODIPY diversification of structurally complex amino acids and peptides was accomplished by racemization-free palladium-catalyzed C(sp3 )-H activation. Transformative fluorescence modification proved viable by triazole-assisted C(sp3 )-H arylation in a chemo- and site-selective fashion, providing modular access to novel BODIPY peptide sensors.

Keywords: BODIPY; C(sp3)−H activation; labeling; peptides; triazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Boron Compounds / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Palladium / chemistry
  • Peptides / chemistry*
  • Quantum Theory
  • Triazoles / chemistry

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Amino Acids
  • Boron Compounds
  • Peptides
  • Triazoles
  • Palladium
  • Carbon
  • Hydrogen