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Helicity-Dependent Enzymatic Peptide Cyclization.

Canan Durukan1,2, Jannik Faierson1, Isabel van der Wal1

  • 1Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, Amsterdam, Netherlands.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|April 28, 2025
PubMed
Summary
This summary is machine-generated.

Peptide structure impacts biological activity. Increased rigidity in helical peptides redirects enzymatic cyclization from intramolecular to intermolecular reactions, guiding chemical reactivity.

Keywords:
Sortasehelixmacrocyclizationpeptidomimeticstapled peptide

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Area of Science:

  • Biochemistry
  • Peptide Chemistry
  • Enzymology

Background:

  • Peptide secondary structure is vital for biological function.
  • Conformational flexibility and rigidity are key to peptide bioactivity.
  • Enzymatic cyclization is a powerful tool for peptide modification.

Purpose of the Study:

  • To investigate the influence of peptide alpha-helicity on enzymatic head-to-tail cyclization.
  • To understand how molecular rigidity affects enzymatic reaction pathways.
  • To explore the design principles for peptide-based materials and probes.

Main Methods:

  • Utilized an engineered Sortase enzyme for peptide cyclization.
  • Synthesized peptides with varying degrees of alpha-helicity.
  • Analyzed cyclization products using biochemical assays.

Main Results:

  • Peptides with low alpha-helicity readily formed intramolecular cyclized products.
  • Highly helical peptides exhibited complex cyclization patterns, including cyclic dimer formation.
  • Increased peptide rigidity shifted the enzymatic reaction from intramolecular to intermolecular processes.

Conclusions:

  • Peptide rigidity is a critical determinant of enzymatic cyclization outcomes.
  • Modulating molecular rigidity can redirect enzymatic reactions and control product formation.
  • These findings offer insights for designing novel peptide-derived materials and responsive probes.