title: Histidine-containing peptide catalysts developed by a facile library screening method.
abstract: Although peptide catalysts have a high potential for the use as organocatalysts, the optimization of peptide sequences is laborious and time-consuming. To address this issue, a facile screening method for finding efficient aminocatalysts from a peptide library has been developed. In the screening for the Michael addition of a malonate to an enal, a dye-labeled product is immobilized on resin-bound peptides through reductive amination to visualize active catalysts. This procedure allows for the monitoring of the reactivity of entire peptides without modifying the resin beads beforehand. Peptides containing histidine at an appropriate position were identified by this method. A novel function of the histidyl residue, which enhances the binding of a substrate to the catalyst by capturing an iminium intermediate, was indicated.
authors.affiliation: Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505 (Japan).
authors.forename: Kengo
authors.initials: K
authors.lastname: Akagawa
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Sakai
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Kudo
mesh_terms: D002384:Catalysis; D006639:Histidine / Q000737:chemistry*; D013058:Mass Spectrometry / Q000379:methods; D010455:Peptides / Q000737:chemistry*
chemical_list: D010455:Peptides; D006639:Histidine
keywords: asymmetric synthesis; combinatorial chemistry; heterogeneous catalysis; peptides; screening