Related Experiment Video
Updated: Aug 29, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Enantioselective ester hydrolysis catalyzed by beta-cyclodextrin conjugated with beta-hairpin peptides
Hiroshi Tsutsumi1, Hiroshi Ikeda, Hisakazu Mihara
1Department of Bioengineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.
Abstract:
Designed cyclodextrin-peptide conjugates, which have one or two beta-hairpin peptides, have been synthesized as catalysts for ester hydrolysis. One or two beta-hairpin peptides were located at the primary hydroxyl group side of beta-cyclodextrin so as to arrange two histidine residues that act as a general acid and a general base catalysts and provide the substrate recognition subsite. Kinetic studies revealed that the two-beta-hairpin peptide was more effective than that of the one-beta-hairpin peptide for substrate recognition.
Related Concept Videos
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Esters to β-Ketoesters: Claisen Condensation Mechanism
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

