Conformations of cyclic pentapeptide endothelin receptor antagonists

Int J Pept Protein Res. 1994 Sep;44(3):223-32. doi: 10.1111/j.1399-3011.1994.tb00164.x.

Abstract

The solution conformations in methanol and chloroform of the endothelin A receptor antagonists cyclo(dV-L-dW-dD-P), 1, and cyclo(dV-N alpha-MeL-dW-dD-P), 2, have been studied by NMR spectroscopy at room temperature and below. In these solvents, both peptides were found to have a well defined peptide backbone conformation composed of a type II beta turn at the Leu-D-Trp and a gamma' turn at Pro. This conformation is in agreement with results reported for 1 in other solvents and consistent with the expected location of the N-methyl substituent in that backbone. In methanol, both peptides show NOE and chemical shift evidence of close contact between the Leu and D-Trp side chains. This interaction is greatly reduced or absent in chloroform, and is stronger in methanol at 203 K than at 298 K.

Publication types

  • Comparative Study

MeSH terms

  • Amino Acid Sequence
  • Endothelin Receptor Antagonists*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Oligopeptides / chemistry*
  • Peptides, Cyclic / chemistry*
  • Protein Conformation*
  • Protein Structure, Secondary
  • Solutions
  • Solvents

Substances

  • Endothelin Receptor Antagonists
  • Oligopeptides
  • Peptides, Cyclic
  • Solutions
  • Solvents