title: Opioid peptides. VIII. Synthesis and preliminary biological activity of [D-Phe3]- or [alpha,beta-dehydro-Phe3]dermorphin tetrapeptides.
abstract: We describe the synthesis and preliminary in vitro pharmacological testing of two new tetrapeptide analogues of the opioid heptapeptide dermorphin H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. The replacement of Phe3 by its D-enantiomer was hardly if at all tolerated. The unsaturated analogue carrying the phenyl ring of the delta Phe3 residue in the Z-configuration, was almost inactive.
mesh_terms: D000818:Animals; D004558:Electric Stimulation; D006168:Guinea Pigs; D066298:In Vitro Techniques; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D011487:Protein Conformation; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides; C046442:tyrosyl-alanyl-phenylalanyl-glycinamide; C046443:tyrosyl-alanyl-delta-phenylalanyl-glycinamide