Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media

Tom Willemse, Karolien Van Imp , Rebecca Jane Miriam Goss, Herman W.T. Van Vlijmen, Wim Schepens, Bert U.W. Maes , Steven Ballet

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)
2 Downloads (Pure)

Abstract

The Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.
Original languageEnglish
Pages (from-to)2055-2070
JournalChemCatChem
Volume7
Issue number14
Early online date29 Jun 2015
DOIs
Publication statusPublished - 13 Jul 2015

Keywords

  • Amino acids
  • C-C coupling
  • Palladium
  • Peptides
  • Homogenous catalysis

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