Synthesis of a Bcl9 Alpha-Helix Mimetic for Inhibition of PPIs by a Combination of Electrooxidative Phenol Coupling and Pd-Catalyzed Cross Coupling

Martin Vareka, Benedikt Dahms, Mario Lang, Minh Hao Hoang, Melanie Trobe, Hansjörg Weber, Maximilian H. Hielscher, Siegfried R. Waldvogel*, Rolf Breinbauer*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in which, at first, two phenols undergo electrooxidative dehydrogenative cross-coupling. The resulting 4,4′-biphenol is then activated by conversion to nonaflates, which serve as leaving groups for iterative Pd-catalyzed Suzuki-cross-coupling reactions with suitably substituted pyridine boronic acids. This work, for the first time, demonstrates the synthetic efficiency of using both electroorganic as well as transition-metal catalyzed cross-coupling in the assembly of oligoarene structures.
Original languageEnglish
Article number340
Number of pages9
JournalCatalysts
Volume10
Issue number3
DOIs
Publication statusPublished - Mar 2020

Keywords

  • Alpha-helix
  • Anode
  • CH-activation
  • Cross-coupling
  • Electrosynthesis
  • Oligoarene
  • Peptidomimetics
  • Phenol
  • Protein-protein interactions
  • Triflate

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Fields of Expertise

  • Human- & Biotechnology

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