Conformationally constrained cyclic peptides: powerful scaffolds for asymmetric catalysis

Lifei Zheng; Alessio Marcozzi; Jennifer Y Gerasimov; Andreas Herrmann

doi:10.1002/anie.201403829

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.

Authors

Lifei Zheng¹, Alessio Marcozzi, Jennifer Y Gerasimov, Andreas Herrmann

Affiliation

¹ Department of Polymer Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands) http://www.rug.nl/research/polymer-chemistry-bioengineering/

PMID: 24898630
DOI: 10.1002/anie.201403829

Abstract

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

Substances

Peptides, Cyclic