Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B

Org Biomol Chem. 2013 Nov 21;11(43):7616-20. doi: 10.1039/c3ob41631c.

Abstract

The preparation of Kyn-containing peptides is difficult, owing to the low reactivity of Kyn in the coupling reaction. In this report, Kyn-containing peptides were efficiently obtained via on-resin ozonolysis of the corresponding Trp-containing peptide. In addition, a Kyn-containing cyclic peptide, cyclomontanin B, has been synthesized by this strategy in the combination with serine/threonine ligation (STL)-mediated cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Kynurenine / chemistry*
  • Molecular Conformation
  • Ozone / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Resins, Synthetic / chemistry*
  • Tryptophan / chemistry*

Substances

  • Peptides
  • Peptides, Cyclic
  • Resins, Synthetic
  • cyclomontanin B
  • Kynurenine
  • Ozone
  • Tryptophan