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Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments.

Stéphanie M Guéret1,2, Sasikala Thavam3, Rodrigo J Carbajo4

  • 1Department of Chemical Biology, AstraZeneca-Max Planck Institute Satellite Unit, Max-Planck-Institute of Molecular Physiology, 44227 Dortmund, Germany.

Journal of the American Chemical Society
|February 15, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed PepNats, a novel method using natural product-inspired structures to mimic "hot loop" protein segments. This approach creates conformationally constrained peptides for targeted protein interactions, leading to new therapeutic candidates.

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Area of Science:

  • Medicinal Chemistry
  • Structural Biology
  • Biochemistry

Background:

  • "Hot loop" protein segments are crucial for protein-protein interactions due to their variable structure.
  • Mimicking these dynamic regions is challenging but essential for drug discovery.

Purpose of the Study:

  • To introduce a novel modality, PepNats, for creating conformationally constrained mimics of protein "hot loops".
  • To synthesize and characterize PepNats derived from inducible nitric oxide synthase (iNOS) and human agouti-related protein (AGRP) hot loops.
  • To evaluate the binding affinity and selectivity of these PepNats to their respective biological targets.

Main Methods:

  • Incorporation of natural product (NP)-inspired structures into macrocyclic peptides.
  • Solid-phase synthesis utilizing macrocyclization by imine formation.
  • Stereoselective 1,3-dipolar cycloaddition for conformational constraint.

Main Results:

  • Successfully synthesized macrocyclic PepNats from iNOS and AGRP hot loops.
  • PepNats derived from iNOS showed potent ligand activity for SPRY domain-containing SOCS box protein 2 (SPSB2).
  • PepNats derived from AGRP exhibited selective ligand activity for melanocortin (MC) receptors.

Conclusions:

  • The absolute configuration of NP-inspired fragments dictates the peptide conformation and binding properties.
  • Combining NP scaffolds with peptidic epitopes yields effective hot loop mimics.
  • PepNats represent a promising strategy for developing conformationally constrained peptides with therapeutic potential.