cis-Apa: a practical linker for the microwave-assisted preparation of cyclic pseudopeptides via RCM cyclative cleavage

J Org Chem. 2011 Feb 4;76(3):766-72. doi: 10.1021/jo101629v. Epub 2011 Jan 7.

Abstract

A new linker cis-5-aminopent-3-enoic acid (cis-Apa) was prepared for the synthesis of cyclic pseudopeptides by cyclization-cleavage by using ring-closing methatesis (RCM). We developed a new synthetic pathway for the preparation of the cis-Apa linker that was tested in the cyclization-cleavage process of different RGD peptide sequences. Different macrocyclic peptidomimetics were prepared by using this integrated microwave-assisted method, showing that the readily available cis-Apa amino acid is well adapted as a linker in the cyclization-cleavage process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylglycine / chemistry*
  • Amino Acid Sequence
  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Microwaves
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry*
  • Stereoisomerism

Substances

  • Peptides, Cyclic
  • Allylglycine