2019 Volume 77 Issue 12 Pages 1222-1233
Peptides are recognized as capable asymmetric catalysts, and have a great potential for the application to unique selective reactions. Most of the reported peptide catalysts consist of a few amino acid residues, and their structures are relatively simple. Our group designed peptide catalysts by combining multiple secondary structural units, and found that these peptides with turn and helical motifs were effective to promote various amine-catalyzed reactions enantioselectively. Such turn-helix-type peptides were applicable to the selective reactions that could not be performed with conventional low-molecular-weight catalysts; an enzyme-co-catalyzed reaction, regioselective reduction, diastereoselective cyclopropanation, kinetic resolution of a planar-chiral compound, and desymmetrization reaction to induce planar chirality were attained. We also explored novel peptide scaffolds by the screening of peptide libraries. Histidine-containing peptide catalysts with a substrate-binding ability and a highly active peptide catalyst in aqueous media were successfully developed.
