Synthesis and receptor binding of opioid peptide analogues containing β3‐homo‐amino acids |
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Authors: | Dominika Wilczyńska Piotr Kosson Maria Kwasiborska Andrzej Ejchart Aleksandra Olma |
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Affiliation: | 1. Institute of Organic Chemistry, Technical University of ?ód?, ?eromskiego 116, 90‐924 ?ód?, Poland;2. Medical Research Centre, Polish Academy of Sciences, Pawińskiego 5, 01‐793 Warsaw, Poland;3. Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 01‐793 Warsaw, Poland |
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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 β3‐homo‐amino acid residues, in general resulted in decrease of affinity to opioid receptors. However, the incorporation β3h‐D ‐Ala in position 2 or β3hPhe 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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Keywords: | β 3‐homo‐amino acids β ‐peptides α ,β ‐hybrides of opioid peptides opioid receptor binding conformational studies |
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