Introduction of all-hydrocarbon i,i + 3 staples into α-helices via ring-closing olefin metathesis

Young Woo Kim, Peter S. Kutchukian, Gregory L. Verdine

Research output: Contribution to journalArticlepeer-review

99 Scopus citations

Abstract

The introduction of all-hydrocarbon i,i+3 staples into α-helical peptide scaffolds via ring-closing olefin metathesis (RCM) between two α-methyl,α-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.

Original languageEnglish
Pages (from-to)3046-3049
Number of pages4
JournalOrganic Letters
Volume12
Issue number13
DOIs
StatePublished - 2 Jul 2010

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