Metal ion effects on the cis/trans isomerization equilibrium of proline in short-chain peptides: a solution NMR study

Chembiochem. 2001 Aug 3;2(7-8):524-9. doi: 10.1002/1439-7633(20010803)2:7/8<524::AID-CBIC524>3.0.CO;2-P.

Abstract

The effect of copper(II) ions on the probabilities of existence of the four detectable conformers of the tetrapeptide Tyr-Pro-Phe-Pro (beta-casomorphin 4) in [2H6]DMSO was investigated by 1H NMR spectroscopy. Integration of the Phe-NH signals provided the relative populations in the free state as tt/tc/ct/cc=28:34:29:9 at 293 K (c=cis, t=trans). Copper(II) was shown to bind to all four isomers, yielding complexes with two different structures, depending on the conformation of Pro(2). The interpretation of paramagnetic relaxation rates of Pro(2)-Halpha signals provided the corresponding isomeric probabilities in the metal-bound state as 13:36:20:31. The observed stabilization of the conformation with the lowest probability of existence (cc) may be relevant for the biological role of copper and other metal ions.

MeSH terms

  • Copper / chemistry*
  • Endorphins / chemistry*
  • Models, Molecular
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Peptide Fragments / chemistry*
  • Proline / chemistry*
  • Protein Conformation
  • Solutions
  • Stereoisomerism
  • Thermodynamics

Substances

  • Endorphins
  • Peptide Fragments
  • Solutions
  • beta-casomorphin 4
  • Copper
  • Proline