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Updated: Jun 12, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Introduction of all-hydrocarbon i,i+3 staples into alpha-helices via ring-closing olefin metathesis
Young-Woo Kim1, Peter S Kutchukian, Gregory L Verdine
1Department of Chemistry, Harvard University, Cambridge, Massachusetts 02138, USA.
Abstract:
The introduction of all-hydrocarbon i,i+3 staples into alpha-helical peptide scaffolds via ring-closing olefin metathesis (RCM) between two alpha-methyl,alpha-pentenylglycine residues incorporated at i and i+3 positions, which lie on the same face of the helix, has been investigated. The reactions were found to be highly dependent upon the side-chain stereochemistry of the amino acids undergoing RCM. The i,i+3 stapling system established here provides a potentially useful alternative to the well-established i,i+4 stapling system now in widespread use.
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