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Related Experiment Videos

Beta-alanine containing cyclic peptides with predetermined turned structure. V

V Pavone1, A Lombardi, M Saviano

  • 1Centro Interdipartimentale di Ricerca su Peptidi Bioattivi and CEINGE-Biotecnologie Avanzate, University of Naples, Federico II, Italy.

Biopolymers
|November 1, 1994
PubMed
Summary
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This study details the synthesis and structural analysis of a cyclic hexapeptide, cyclo-(Pro-Phe-beta-Ala-Phe-Phe-beta-Ala). Results show beta-alanyl residues have a low propensity for turned structures in this peptide.

Area of Science:

  • Peptide Chemistry
  • Structural Biology
  • Organic Synthesis

Background:

  • Cyclic peptides offer diverse structural motifs.
  • Understanding peptide conformation is crucial for drug design.

Purpose of the Study:

  • To synthesize and characterize the cyclic hexapeptide cyclo-(Pro-Phe-beta-Ala-Phe-Phe-beta-Ala).
  • To elucidate its solid-state and solution conformations.
  • To investigate the role of beta-alanine residues in peptide structure.

Main Methods:

  • Classical solution phase peptide synthesis.
  • N,N-dicyclohexyl-carbodiimide mediated cyclization.
  • Single crystal X-ray diffraction analysis.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (1H, 13C, 2D techniques).

Related Experiment Videos

  • Rotating frame nuclear Overhauser effect spectroscopy (ROESY).
  • Restrained molecular dynamics simulations.

    • Main Results:

    • The cyclic hexapeptide was synthesized and purified.
    • Solid-state structure revealed a cis beta-Ala6-Pro1 peptide bond and beta-turns.
    • NMR and molecular dynamics showed two slowly interconverting conformers in solution due to cis-trans isomerism.
    • Beta-alanyl residues were found at positions with low propensity for forming turns.

    Conclusions:

    • The study provides a detailed structural characterization of the cyclic hexapeptide.
    • Confirms the low propensity of beta-alanine for turn formation in cyclic peptides.
    • Highlights the conformational flexibility in solution due to peptide bond isomerism.