Synthesis and evaluation of α-helix mimetics based on a trans-fused polycyclic ether: sequence-selective binding to aspartate pairs in α-helical peptides

Hiroki Oguri, Shintaro Tanabe, Akifumi Oomura, Mitsuo Umetsu, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Inspired by the topological similarity between ladder-like cyclic ether skeletons and α-helical peptides, a trans-fused 6/6/6/6 tetracyclic ether containing two hydroxyl groups separated by a distance of 4.8 Å was designed as a scaffold for a nonpeptidic α-helix mimetic. Two alkyl guanidinium groups were attached to the hydroxyl groups to develop a synthetic receptor for the specific recognition of i + 4 spaced aspartate pairs on the surface of an α-helical peptide. A circular dichroism (CD) titration showed that this mode of molecular recognition stabilizes α-helical structures of peptides containing i + 4 spaced aspartate pairs.

Original languageEnglish
Pages (from-to)5801-5805
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number32
DOIs
Publication statusPublished - 2006 Aug 7

Keywords

  • Molecular recognition
  • Polycyclic ether
  • Scaffold
  • α-Helix mimetic

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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