Pseudoprolines as removable turn inducers: tools for the cyclization of small peptides

J Org Chem. 2004 Dec 10;69(25):8804-9. doi: 10.1021/jo0484732.

Abstract

The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Models, Molecular
  • Molecular Conformation
  • Peptides / chemical synthesis*
  • Proline / analogs & derivatives*
  • Proline / chemistry*

Substances

  • Peptides
  • Proline