Highly Enantioselective Enone Epoxidation Catalyzed by Short Solid Phase-Bound Peptides: Dominant Role of Peptide Helicity

2001/11/01 by Albrecht Berkessel, Norbert Gasch, Katja Glaubitz +1 · 3 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Engineering · #Chemical Synthesis and Analysis #Click Chemistry and Applications #Surface Chemistry and Catalysis

paper · doi:10.1021/ol0166451

openalex publication_date 2001/11/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The series of L-Leu 1-20-mers, peptides carrying 1-5 N-terminal Gly residues, and oligomers of (S)-beta(3)-Leu and (1R,2R)-2-aminocyclohexanecarboxylic acid were synthesized on TentaGel S NH(2). Five L-Leu residues were found sufficient to catalyze the Juliá-Colonna epoxidation of chalcone with 96-98% ee. Experiment and molecular modeling suggest that catalysis is effected by binding of the enone to the N-terminus, and the helicity of the peptide determines the epoxide configuration through face-selective delivery of a hydroperoxide anion. [reaction: see text]

Citations

• Towards a mechanistic insight into the Juliá-Colonna asymmetric epoxidation of α,β-unsaturated ketones using discrete lengths of poly-leucine

Cited by

• Novel conditions for the Juliá–Colonna epoxidation reaction providing efficient access to chiral, nonracemic epoxides
• Asymmetric Epoxidation of Electron‐Deficient Alkenes
• Juliá–Colonna epoxidation [wikipedia]