Conformationally constrained cyclic peptides: powerful scaffolds for asymmetric catalysis

Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7599-603. doi: 10.1002/anie.201403829. Epub 2014 Jun 4.


Cyclic peptides containing a disulfide bridge were identified as a simple and versatile coordination sphere for asymmetric catalysis. Upon complexation with Cu(2+) ions they catalyze Diels-Alder and Friedel-Crafts reactions with high enantioselectivities of up to 99% ee and 86% ee, respectively. Moreover, the peptides ligands were systematically optimized with the assistance of "Alanine Scanning". This biomolecular design could greatly expand the choice of peptide scaffolds for artificial metallopeptide catalysts.

Keywords: Diels-Alder reaction; Friedel-Crafts reaction; asymmetric catalysis; peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Catalysis
  • Molecular Sequence Data
  • Peptides, Cyclic / chemistry*
  • Protein Conformation


  • Peptides, Cyclic