Chemical Synthesis of a Potent Antimicrobial Peptide Murepavadin Using a Tandem Native Chemical Ligation/Desulfurization Reaction

J Org Chem. 2021 Nov 5;86(21):15242-15246. doi: 10.1021/acs.joc.1c01858. Epub 2021 Oct 12.

Abstract

Classical approaches for the backbone cyclization of polypeptides require conditions that may compromise the chirality of the C-terminal residue during the activation step of the cyclization reaction. Here, we describe an efficient epimerization-free approach for the Fmoc-based synthesis of murepavadin using intramolecular native chemical ligation in combination with a concomitant desulfurization reaction. Using this approach, bioactive murepavadin was produced in a good yield in two steps. The synthetic peptide antibiotic showed potent activity against different clinical isolates of P. aeruginosa. This approach can be easily adapted for the production of murepavadin analogues and other backbone-cyclized peptides.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimicrobial Peptides* / chemical synthesis
  • Antimicrobial Peptides* / pharmacology
  • Peptides, Cyclic* / chemical synthesis
  • Peptides, Cyclic* / pharmacology
  • Pseudomonas aeruginosa

Substances

  • Antimicrobial Peptides
  • Peptides, Cyclic
  • murepavadin