Helical peptaibol mimics are better ionophores when racemic than when enantiopure

Org Biomol Chem. 2015 Oct 7;13(37):9580-4. doi: 10.1039/c5ob01652e.

Abstract

Helical peptide foldamers rich in α-aminoisobutyric acid (Aib) act as peptaibol-mimicking ionophores in the phospholipid bilayers of artificial vesicles. Racemic samples of these foldamers are more active than their enantiopure counterparts, which was attributed to differing propensities to form aggregates with crystal-like features in the bilayer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminobutyrates / chemistry
  • Ionophores / chemistry*
  • Ionophores / pharmacology*
  • Lipid Bilayers / chemistry
  • Lipid Bilayers / metabolism
  • Models, Molecular
  • Molecular Conformation
  • Peptaibols / chemistry*
  • Peptidomimetics / chemistry*
  • Peptidomimetics / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Aminobutyrates
  • Ionophores
  • Lipid Bilayers
  • Peptaibols
  • Peptidomimetics
  • alpha-aminobutyric acid