Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium-Mediated Cross-Coupling

Dowine de Bruijn, Gerard Roelfes

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Abstract

Dehydroalanine (Dha) is a remarkably versatile non-canonical amino acid often found in antimicrobial peptides. Here we present the catalytic modification of Dha via a palladium mediated cross coupling reaction. Using Pd(EDTA)(OAc)2 as water soluble catalyst, a variety of arylboronic acids was coupled to the dehydrated residues in proteins and peptides such as nisin. The cross coupling reaction yields both the Heck product, in which the sp2-hybridisation of the α-carbon is retained, as well as the conjugated addition product. The reaction can be performed under mild aqueous conditions, which makes this method an attractive addition to the palette of bio-orthogonal catalytic methods.

Original languageEnglish
Pages (from-to)12728-12733
JournalChemistry
Volume24
Issue number48
Early online date19-Jun-2018
DOIs
Publication statusPublished - Aug-2018

Keywords

  • bio-orthogonal catalysis
  • cross-coupling
  • dehydroalanine
  • Nisin
  • palladium
  • OXIDATIVE HECK REACTION
  • AMINO-ACIDS
  • MASS-SPECTROMETRY
  • NISIN
  • BIOSYNTHESIS
  • ARYLATION
  • INTERCONVERSION
  • THIOSTREPTON
  • UBIQUITIN
  • LIGATION

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