Aziridine-Mediated Ligation at Phenylalanine and Tryptophan Sites

Chem Asian J. 2017 Aug 4;12(15):1869-1874. doi: 10.1002/asia.201700538. Epub 2017 Jun 26.

Abstract

An efficient approach towards peptide synthesis that allows easy access to variety of small peptides via one-pot aziridine-mediated ligation/desulfurization strategy has been described. The protocol afforded a library of phenylalanine- and tryptophan-containing α-peptides in good yields by regioselective ring-opening of aziridine-3-aryl-2-carboxylates with peptide thioacids, followed by desulfurization.

Keywords: amino acids; aziridines; desulfurization; ligation; peptides.

MeSH terms

  • Aziridines / chemistry*
  • Chemistry Techniques, Analytical*
  • Peptide Library
  • Peptides / chemical synthesis*
  • Phenylalanine / chemistry*
  • Stereoisomerism
  • Tryptophan / chemistry*

Substances

  • Aziridines
  • Peptide Library
  • Peptides
  • Phenylalanine
  • Tryptophan