Chemical labeling strategy with (R)- and (S)-trifluoromethylalanine for solid state 19F NMR analysis of peptaibols in membranes

J Am Chem Soc. 2009 Nov 4;131(43):15596-7. doi: 10.1021/ja9067595.

Abstract

Substitution of a single Aib-residue in a peptaibol with (R)- and (S)-trifluoromethylalanine yields two local orientational constraints theta by solid state (19)F NMR. The structure of the membrane-perturbing antibiotic alamethicin in DMPC bilayers was analyzed in terms of two angles tau and rho from six such constraints, showing that the N-terminus (up to a kink at Pro14) is folded as an alpha-helix, tilted away from the membrane normal by 8 degrees, and assembled as an oligomer. The new (19)F NMR label CF(3)-Ala has thus been demonstrated to be highly sensitive, virtually unperturbing, and ideally suited to characterize peptaibols in membranes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry
  • Circular Dichroism
  • Fluorine / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Peptaibols / chemistry*
  • Stereoisomerism

Substances

  • Peptaibols
  • alpha-trifluoromethylalanine
  • Fluorine
  • Alanine