Peptide ligation from alkoxyamine based radical addition


  • Trimaille Thomas
  • Autissier Laurent
  • Rakotonirina Mamy Daniel
  • Guillaneuf Yohann
  • Villard Claude
  • Bertin Denis
  • Gigmes Didier
  • Mabrouk Kamel

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Intermolecular radical 1,2-addition (IRA) of N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (SG1) based alkoxyamines onto activated olefins is used as a tool for peptide ligation. This strategy relies on simple peptide pre-derivatization to obtain (i) a SG1 nitroxide functionalized resin peptide at its N-terminus (SG1-peptide alkoxyamine), (ii) a vinyl functionalized peptide (either at its C-terminus or N-terminus), and does not require any coupling agents.

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