Journal
ORGANIC LETTERS
Volume 12, Issue 13, Pages 3046-3049Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1010449
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Funding
- Harvard & Dana-Farber Program in Cancer Chemical Biology
- NSF
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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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