Conformational analysis and mu-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent

Org Biomol Chem. 2003 Sep 7;1(17):3010-4. doi: 10.1039/b306161m.

Abstract

Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbamates / chemistry
  • Carbamates / pharmacology
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology
  • Protein Conformation
  • Rats
  • Receptors, Opioid, mu / drug effects*
  • Solvents / chemistry
  • Spectrophotometry, Infrared
  • Temperature

Substances

  • Carbamates
  • Ligands
  • Oligopeptides
  • Receptors, Opioid, mu
  • Solvents
  • endomorphin 1