Experimental simulation of the environment of the delta opioid receptor. A 500 MHz study of enkephalins in CDCl3

Biochem Biophys Res Commun. 1984 Jun 15;121(2):456-62. doi: 10.1016/0006-291x(84)90204-3.

Abstract

Complexes of [Met5] and [Leu5]enkephalin amides with 18-crown-6-ether have been studied in CDCl3 solution by means of 500 MHz NMR spectroscopy, in order to simulate two of the features of the opioid receptor: the apolar environment and the binding of the charged N atom. Contrary to all previous studies in polar solvents the NH resonances are spread in a huge range (ca. 4 ppm) as in the spectra of rigid cyclic peptides. The two observed intramolecular hydrogen bonds are consistent with the existence of a single, folded, conformation, i.e. a C10 beta-turn in which the Phe4 NH is linked to the Tyr1 CO group.

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Chloroform
  • Crown Ethers*
  • Energy Transfer
  • Enkephalins / metabolism*
  • Ethers, Cyclic
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Protein Conformation
  • Protons
  • Receptors, Opioid / metabolism*
  • Receptors, Opioid, delta
  • Solutions
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Crown Ethers
  • Enkephalins
  • Ethers, Cyclic
  • Protons
  • Receptors, Opioid
  • Receptors, Opioid, delta
  • Solutions
  • 18-crown-6
  • Chloroform