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Related Experiment Videos

Bicyclic tripeptide mimetics with reverse turn inducing properties.

P Johannesson1, G Lindeberg, W Tong

  • 1Department of Organic Pharmaceutical Chemistry, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden.

Journal of Medicinal Chemistry
|March 3, 1999
PubMed
Summary

Researchers synthesized novel bicyclic peptide analogues of angiotensin II. These compounds, designed with specific beta-turn geometries, showed no affinity for the angiotensin II AT1 receptor, suggesting potential for new therapeutic strategies.

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Area of Science:

  • Medicinal Chemistry
  • Peptide Chemistry
  • Pharmacology

Background:

  • Angiotensin II is a key peptide hormone regulating blood pressure.
  • Development of angiotensin II analogues is crucial for understanding its function and for therapeutic interventions.
  • Constrained peptide structures can mimic or block peptide-receptor interactions.

Purpose of the Study:

  • To synthesize novel bicyclic analogues of angiotensin II.
  • To investigate the conformational properties and receptor binding of these analogues.
  • To explore the potential of nonclassical beta-turn geometries in peptide design.

Main Methods:

  • Synthesis of 5,8-bicyclic and 5,9-bicyclic tripeptide units.
  • Theoretical conformational analysis to predict peptide geometries.

Related Experiment Videos

  • Acid-catalyzed deprotection and spontaneous bicyclization of model peptides.
  • Assessment of receptor binding affinity for the angiotensin II AT1 receptor.

    • Main Results:

    • Successfully synthesized novel bicyclic angiotensin II analogues.
    • Demonstrated a preference for C-terminal bicyclization in model peptides.
    • The synthesized bicyclic thiazolidine-related analogues exhibited no affinity for the angiotensin II AT1 receptor.

    Conclusions:

    • Novel constrained bicyclic peptide analogues of angiotensin II were synthesized.
    • The synthesized analogues do not interact with the angiotensin II AT1 receptor.
    • These findings may guide the development of new therapeutic agents targeting the renin-angiotensin system.