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Keywords:

  • alkylation;
  • amino acids;
  • peptide modification;
  • phase-transfer catalysis;
  • phosphonium salts
Thumbnail image of graphical abstract

Dual-purpose activation: Peptide C-terminal azlactones I undergo stereoselective alkylation with high efficiency by the use of a newly devised chiral tetraaminophosphonium salt as a phase-transfer catalyst, and the alkylated azlactone products II can be employed directly for peptide ligation (see scheme, LG=leaving group). In this way, a wide range of chiral quaternary α-amino acid residues can be incorporated at specific sites of a peptide strand.