Summary
Using the method of conformational constraint, we have designed and synthesized analogues of deltorphin I containing each of the four stereoisomers of the unusual amphiphilic amino acid β-hydroxyphenylalanine in position 3. The potency and selectivity of these analogues were evaluated by radioreceptor binding assays and by bioassay in MVD and GPI. The results show that introducing a hydrophilic group into the β-carbon of Phe3 decreases the affinity and biological activity of δ-opioid receptors, which strongly depend on the chirality of the α-carbon, but not on that of the β-carbon.
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Misicka, A., Lipkowski, A.W., Stropova, D. et al. Amino acids with amphiphilic side chains: Deltorphin analogues with Phe3 replaced by all β-hydroxyphenylalanine diastereoisomers. Lett Pept Sci 2, 203–205 (1995). https://doi.org/10.1007/BF00119153
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DOI: https://doi.org/10.1007/BF00119153