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Nmr studies of a series of dehydrodermorphins

✍ Scribed by Maria A. Castiglione-Morelli; Gabriella Saviano; Piero A. Temussi; Gianfranco Balboni; Severo Salvadori; Roberto Tomatis

Publisher
Wiley (John Wiley & Sons)
Year
1989
Tongue
English
Weight
479 KB
Volume
28
Category
Article
ISSN
0006-3525

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✦ Synopsis

The third and fifth aromatic residues of dermorphin, a potent p-opioid peptide, and of its N-terminal fragments, from the pentapeptide to the parent heptapeptide amide, have been systematically substituted with Z-dehydrophenylalanine ( A-Phe) and/or Phe to investigate the conformation-activity relationship.

The characterization in DMSO-d, at 500 MHz indicates that, in this solvent, all peptides adopt essentially random, extended conformations, as a consequence of the strong solvation. The chemical shift of the methyl group of D-Na is influenced by the precise orientation of the side chain of the third residue in a fashion that can be correlated to the p potency, consistently with our model of preceptor.

However, the complexes of the pentapeptides with 18-crown-6-ether, when dissolved in chloroform, adopt ordered, folded conformations, a behavior that closely parallels the CD observations in methanol.

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