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Area of Science:

  • Medicinal Chemistry
  • Biochemistry
  • Molecular Biology

Background:

  • Solid-phase peptide synthesis using racemic amino acids produces stereorandomized peptides.
  • Stereorandomization modulates the activity, toxicity, and stability of membrane-disruptive antimicrobial peptides (AMPs) and dendrimers.
  • The proline-rich AMP oncocin inhibits bacterial ribosomes and is a target-binding peptide.

Purpose of the Study:

  • To investigate the compatibility of stereorandomization with target-binding peptides using oncocin as an example.
  • To determine if stereorandomization affects oncocin's ribosome binding, antibacterial activity, and mechanism of action.

Main Methods:

  • Solid-phase peptide synthesis of stereorandomized oncocin variants.
  • High-performance liquid chromatography (HPLC) for purification.
  • Assessment of ribosome binding and antibacterial activity against drug-resistant bacteria.
  • Evaluation of serum degradation and peptide uptake mechanisms.

Main Results:

  • Stereorandomization of up to nine C-terminal residues preserved oncocin's ribosome binding and antibacterial effects.
  • Stereorandomized oncocin variants showed protection against serum degradation.
  • Fully stereorandomized oncocin exhibited antibacterial activity via an alternative mechanism, independent of ribosome binding.
  • Stereorandomization facilitated peptide uptake in dilute media.

Conclusions:

  • Stereorandomization is compatible with target-binding peptides like oncocin.
  • Stereorandomization can maintain or alter the mechanism of action of peptides.
  • This approach aids in understanding peptide mechanisms and developing novel therapeutics.