Site-specific integration of amino acid fragments into cyclic peptides

J Am Chem Soc. 2014 Mar 12;136(10):3728-31. doi: 10.1021/ja412256f. Epub 2014 Feb 26.

Abstract

The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amino Acids / chemistry*
  • Aziridines / chemistry*
  • Peptide Fragments / chemistry*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry

Substances

  • Amides
  • Amino Acids
  • Aziridines
  • Peptide Fragments
  • Peptides, Cyclic
  • aziridine