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Letters in Peptide Science

, Volume 5, Issue 5–6, pp 437–440 | Cite as

Consequences of cis-amide bond simulation in opioid peptides

  • Jacek Olczak
  • Krzysztof Kaczmarek
  • Iwona Maszczyńska
  • Marek Lisowski
  • Dagmar Stropova
  • Victor J. Hruby
  • Henry I. Yamamura
  • Andrzej W. Lipkowski
  • Janusz Zabrocki
Article
  • 36 Downloads

Summary

Six analogs of leucine-enkephalin were synthesized in which a 1,5-disubstituted tetrazole ring was incorporated in order to lock selected peptide bonds in cis geometry. The obtained compounds were examined based on their biological effects in vivo and in vitro. Only one analog was completely inactive in binding assays being very weakly active in the antinociceptive test. The remaining five compounds displayed at least weak receptor affinity and in vivo activity.

Key words

cis peptide bond conformation 1,5-disubstituted tetrazole ring Leu-enkephalin 

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Copyright information

© Kluwer Academic Publishers 1998

Authors and Affiliations

  • Jacek Olczak
    • 1
  • Krzysztof Kaczmarek
    • 1
  • Iwona Maszczyńska
    • 2
  • Marek Lisowski
    • 3
  • Dagmar Stropova
    • 4
  • Victor J. Hruby
    • 5
  • Henry I. Yamamura
    • 4
  • Andrzej W. Lipkowski
    • 2
  • Janusz Zabrocki
    • 1
  1. 1.Institute of Organic ChemistryTechnical University of łódźłódźPoland
  2. 2.Medical Research CentrePolish Academy of SciencesWarsawPoland
  3. 3.Institute of ChemistryUniversity of WrocławWrocławPoland
  4. 4.Department of PharmacologyUniversity of ArizonaTucsonU.S.A.
  5. 5.Department of ChemistryUniversity of ArizonaTucsonU.S.A.

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