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Highly potent side-chain to side-chain cyclized enkephalin analogues containing a carbonyl bridge: synthesis, biology and conformation

✍ Scribed by Danuta Pawlak; Marta Oleszczuk; Jacek Wójcik; Maria Pachulska; Nga N. Chung; Peter W. Schiller; Jan Izdebski

Book ID
105360069
Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
279 KB
Volume
7
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

Six novel cyclic enkephalin analogues have been synthesized. Cyclization of the linear peptides containing basic amino acid residues in position 2 and 5 was achieved by treatment with bis(4‐nitrophenyl)carbonate. It was found that some of the compounds exibit unusually high µ‐opioid activity in the guinea pig ileum (GPI) assay. The 18‐membered analogue cyclo(N^ε^,N^β__′__^‐carbonyl‐𝒹‐Lys^2^,Dap^5^)enkephalinamide turned out to be one of the most potent µ‐agonists reported so far. NMR spectra of the peptides were recorded and structural parameters were determined. The conformational space was exhaustively examined for each of them using the electrostatically driven Monte Carlo method. Each peptide was finally described as an ensemble of conformations. A model of the bioactive conformation of this class of opioid peptides was proposed. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.

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