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Updated: Aug 7, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: dominant role of peptide
A Berkessel1, N Gasch, K Glaubitz
1Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany. berkessel@uni-koeln.de
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]
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