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Synthesis and receptor binding of opioid peptide analogues containing β3-homo-amino acids

✍ Scribed by Dominika Wilczyńska; Piotr Kosson; Maria Kwasiborska; Andrzej Ejchart; Aleksandra Olma

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
136 KB
Volume
15
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

β‐Amino acids containing hybrid peptides and β‐peptides show great potential as peptidomimetics. In this paper we describe the synthesis and affinity toward the µ‐ and δ‐opioid receptors of β‐peptides, analogues of Leu‐enkephalin, deltorphin I, dermorphin and α,β‐hybrides, analogues of deltorphin I. Substitution of α‐amino acid residues with β^3^‐homo‐amino acid residues, in general resulted in decrease of affinity to opioid receptors. However, the incorporation β^3^h‐D‐Ala in position 2 or β^3^__h__Phe in position 3 of deltorphin I resulted in potent and selective ligand for δ‐opioid receptor. The NMR studies of β‐deltorphin I analogue suggest that conformational motions in the central part of the peptide backbone are partially restricted and some conformational preferences can be expected. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd.

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