Dehydro‐enkephalins. III. Synthesis and biological activity of [ΔAla2, Leu5]‐enkephalin
- 12 January 1982
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 19 (1), 54-62
- https://doi.org/10.1111/j.1399-3011.1982.tb03022.x
Abstract
[.DELTA.Ala2, Leu5]-enkephalin was prepared and was more active than the parent saturated enkephalin in a binding assay using rat brain membranes and [3H]dihydromorphine as a tracer. In a comparison of potencies against [3H]dihydromorphine and [3H]-[D-Ala2, D-Leu5]-enkephalin as tracers, [.DELTA.Ala2, Leu5]-enkephalin showed preference for .mu. opiate receptors, possibly due to the hydrophobicity of the .DELTA.Ala2 residue. A synthetic tetrapeptide enkephalin [.DELTA.Ala2]-desLeu5-enkephalin had weak activity and high selectivity for the .mu. receptors. O-Acylation of a serine residue in the peptide was achieved by coupling between the peptide and a carboxylic acid using N,N''-dicyclohexylcarbodiimide and a catalytic amount of 4-dimethylaminopyridine.Keywords
This publication has 22 references indexed in Scilit:
- Structure-NCS activity studies with the enkephalinsPharmacology & Therapeutics, 1980
- Structure-Activity Relationships of Enkephalin-Like PeptidesAnnual Review of Pharmacology and Toxicology, 1980
- Opiate activity of [DAla2,ΔzPhe4]-methionine-enkephalinamideBiochemical and Biophysical Research Communications, 1979
- D-Ala2, ΔzPhe4-methionine enkephalin amide, a dehydropeptide hormoneBiochemical and Biophysical Research Communications, 1978
- An Analog of Enkephalin Having Prolonged Opiate-Like Effects in VivoScience, 1977
- Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogs with L-3,4-dehydroproline in position 7Journal of Medicinal Chemistry, 1977
- Synthesis and opioid activities of stereoisomers and other D-amino acid analogs of methionine-enkephalinBiochemical and Biophysical Research Communications, 1976
- [D-Ala 2 ]-Met-Enkephalinamide: A Potent, Long-Lasting Synthetic Pentapeptide AnalgesicScience, 1976
- Mode of deactivation of the enkephalins by rat and human plasma and rat brain homogenatesNature, 1976
- Über ein allgemeines Verfahren der Peptid‐SyntheseBerichte der deutschen chemischen Gesellschaft (A and B Series), 1932