Design and synthesis of simplified polycyclic ethers and evaluation of their interaction with an α-helical peptide as a model of target proteins

Makoto Sasaki, Kazuo Tachibana

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Two simplified pentacyclic ethers, having 6/7/6/6/7 and 6/7/6/7/7 ring systems, were synthesized. A convergent route based on the Suzuki-Miyaura cross-coupling strategy was applied to synthesize these two compounds. Interactions between α-helical peptide, melittin, and synthesized pentacyclic ethers were evaluated by circular dichroism (CD) spectroscopy. Interestingly, only the polycyclic ether having a 6/7/6/7/7 ring stabilized the α-helical structure of melittin. This result indicated that a ring fusion manner of the polycyclic structure is important to recognize membrane proteins.

Original languageEnglish
Pages (from-to)3181-3186
Number of pages6
JournalTetrahedron Letters
Volume48
Issue number18
DOIs
Publication statusPublished - 2007 Apr 30
Externally publishedYes

Keywords

  • Convergent synthesis
  • Polycyclic ether
  • Simplified ring system
  • Suzuki-Miyaura cross coupling
  • α-Helix

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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