Conformational sampling of bioactive conformers: a low-temperature NMR study of 15N-Leu-enkephalin

J Pept Sci. 1998 Jun;4(4):253-65. doi: 10.1002/(SICI)1099-1387(199806)4:4%3C253::AID-PSC142%3E3.0.CO;2-P.

Abstract

Conformational studies of enkephalins are hampered by their high flexibility which leads to mixtures of quasi-isoenergetic conformers in solution and makes NOEs very difficult to detect in NMR spectra. In order to improve the quality of the NMR data, Leu-enkephalin was synthesized with 15N-labelled uniformly on all amide nitrogens and examined in a viscous solvent medium at low temperature. HMQC NOESY spectra of the labelled Leu-enkephalin in a DMSOd6/H2O) mixture at 275 K do show numerous NOEs, but these are not consistent with a single conformer and are only sufficient to describe the conformational state as a mixture of several conformers. Here a different approach to the structure-activity relationships of enkephalins is presented: it is possible to analyse the NMR data in terms of limiting canonical structures (i.e. beta- and gamma-turns) and finally to select only those consistent with the requirements of delta selective agonists and antagonists. This strategy results in the prediction of a family of conformers that may be useful in the design of new delta selective opioid peptides.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cold Temperature
  • Enkephalin, Leucine / chemistry*
  • Enkephalin, Leucine / physiology
  • Magnetic Resonance Spectroscopy / methods*
  • Models, Molecular
  • Nitrogen Isotopes
  • Protein Conformation*
  • Software
  • Structure-Activity Relationship
  • Torsion Abnormality

Substances

  • Nitrogen Isotopes
  • Enkephalin, Leucine