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Amino Acids

, Volume 39, Issue 5, pp 1589–1593 | Cite as

Compatibility of the conformationally rigid CF3-Bpg side chain with the hydrophobic coiled-coil interface

  • Mario Salwiczek
  • Pavel K. Mikhailiuk
  • Sergii Afonin
  • Igor V. Komarov
  • Anne S. Ulrich
  • Beate KokschEmail author
Short Communication

Abstract

3-(Trifluoromethyl)bicyclopent-[1.1.1]-1-yl glycine (CF3-Bpg) has previously been established as a useful 19F NMR label to analyse the structures of oligomeric membrane-active peptides or transmembrane segments. To systematically examine the effect of side chain volume, conformational rigidity, and hydrophobicity of CF3-Bpg in polypeptide environments the amino acid was incorporated into an established coiled-coil based screening system. A single substitution of either valine (position a16) or leucine (position d19) within the hydrophobic core of the heteromeric coiled coil has practically no effect on its structure. Despite its comparatively high hydrophobicity, however, the stiff and bulky side chain of CF3-Bpg is not so well accommodated by the hydrophobic core as it leads to a more pronounced destabilization than observed for other, more polar fluorinated amino acids which carry more flexible side chains. CF3-Bpg is therefore a useful 19F NMR label, though not for monitoring the stability of such helix–helix interactions.

Keywords

Fluorinated amino acids CF3-Bicyclopentyl glycine α-Helical coiled coil Solid state 19F NMR 19F labelling 

Notes

Acknowledgments

This research was supported by Deutsche Forschungsgemeinschaft (KO 1976/2-2). We are furthermore grateful to Allison Berger for proofreading of the manuscript.

Supplementary material

726_2010_581_MOESM1_ESM.doc (501 kb)
Supplementary material 1 (DOC 501 kb)

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Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Mario Salwiczek
    • 1
  • Pavel K. Mikhailiuk
    • 2
  • Sergii Afonin
    • 3
  • Igor V. Komarov
    • 2
  • Anne S. Ulrich
    • 3
  • Beate Koksch
    • 1
    Email author
  1. 1.Department of Biology, Chemistry, Pharmacy, Institute of Chemistry and BiochemistryFreie Universität BerlinBerlinGermany
  2. 2.Department of ChemistryKyiv National Taras Shevchenko UniversityKievUkraine
  3. 3.Karlsruhe Institute of Technology (KIT)Institute of Biological Interfaces (IBG2) and Institute of Organic ChemistryKarlsruheGermany

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