Abstract

Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition-metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C-H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user-friendly synthesis, common Pd(II) sources, and a more cost-effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.
Original languageEnglish
Article numbere202104385
JournalChemistry - A European Journal
Volume28
Issue number11
Early online date14 Dec 2021
DOIs
Publication statusPublished - 21 Feb 2022

Keywords

  • C−H activation
  • bioconjugation
  • cross-coupling
  • cysteine
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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