Conformational characteristics of receptor-selective opioid peptides. 1H n.m.r. and c.d. spectroscopic studies of delta-kephalin and [Val4]morphiceptin

Biochem J. 1988 Apr 15;251(2):581-8. doi: 10.1042/bj2510581.

Abstract

An investigation on the conformations of highly receptor-selective opioid peptides was carried out to gain further understanding of the structure-activity relationship of endogenous enkephalins. The preferred conformations of a highly mu-selective [Val4]morphiceptin and a highly delta-selective delta-kephalin have been probed by 1H n.m.r. solvent-, concentration- and temperature-dependences of amide protons to take the folded conformations stabilized by an intramolecular hydrogen bond and the anti-parallely extended dimeric structures respectively. Their possible stereo-conformations were proposed, based on the analyses of the vicinal coupling constants (JHNC alpha H). The conformational difference between the mu- and delta-selective opioid peptides was further ascertained by the c.d. measurements. The c.d. spectra of the mu-selective peptides show negative bands in the range of 210-230 nm, while those of the delta-selective ones show the opposite positive bands. A correlation between c.d. spectra and receptor-selectivity was possible.

MeSH terms

  • Circular Dichroism
  • Endorphins*
  • Enkephalins
  • Magnetic Resonance Spectroscopy
  • Oligopeptides*
  • Protein Conformation
  • Receptors, Opioid*
  • Solvents
  • Temperature

Substances

  • Endorphins
  • Enkephalins
  • Oligopeptides
  • Receptors, Opioid
  • Solvents
  • deltakephalin
  • morphiceptin