Straightforward synthesis of cyclic and bicyclic peptides

Org Lett. 2013 Apr 19;15(8):2038-41. doi: 10.1021/ol400726y. Epub 2013 Apr 9.

Abstract

Cyclic peptide architectures can be easily synthesized from cysteine-containing peptides with appending maleimides, free or protected, through an intramolecular Michael-type reaction. After peptide assembly, the peptide can cyclize either during the trifluoroacetic acid treatment, if the maleimide is not protected, or upon deprotection of the maleimide. The combination of free and protected maleimide moieties and two orthogonally protected cysteines gives access to structurally different bicyclic peptides with isolated or fused cycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cysteine / chemistry*
  • Maleimides / chemistry
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry

Substances

  • Maleimides
  • Peptides
  • Peptides, Cyclic
  • maleimide
  • Cysteine