Amino acids with amphiphilic side chains: Deltorphin analogues with Phe3 replaced by all β-hydroxyphenylalanine diastereoisomers

Aleksandra Misicka, Andrzej W. Lipkowski, Dagmar Stropova, Peg Davis, Frank Porreca, Henry I. Yamamura, Victor J Hruby

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)203-205
Number of pages3
JournalLetters in Peptide Science
Volume2
Issue number3-4
DOIs
Publication statusPublished - Nov 1995

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Keywords

  • β-Hydroxyphenylalanine
  • Deltorphin
  • Opioids

ASJC Scopus subject areas

  • Biochemistry

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