Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Comparison of Oct-2-enyl and Oct-4-enyl Staples for Their Formation and α-Helix Stabilizing Effects

  • Pham, Thanh K. (College of Pharmacy, Dongguk University) ;
  • Yoo, Jiyeon (College of Pharmacy, Dongguk University) ;
  • Kim, Young-Woo (College of Pharmacy, Dongguk University)
  • Received : 2013.04.24
  • Accepted : 2013.06.10
  • Published : 2013.09.20
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Abstract

The all-hydrocarbon i,i+4 stapling system using an oct-4-enyl crosslink is one of the most widely employed chemical tools to stabilize an ${\alpha}$-helical conformation of a short peptide. This crosslinking system has greatly extended our ability to modulate intracellular protein-macromolecule interactions. The helix-inducing property of the i,i+4 staple has shown to be highly dependent on the length and the stereochemistry of the oct-4-enyl crosslink. Here we show that changing the double bond position within the i,i+4 staple has a considerable impact not only on the formation of the crosslink but also on ${\alpha}$-helix induction. The data further increases the understanding of the structure-activity relationships of this valuable chemical tool.

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References

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