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Chirality Effects in Peptide-Based Dynamic Combinatorial Chemistry.

Alice Gable1, Emmi Pohjolainen1, Gerrit Groenhof1

  • 1Department of Chemistry, Nanoscience Center, University of Jyväskylä, Survontie 9 C, Jyväskylä, 40014, Finland.

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|May 13, 2025
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Summary
This summary is machine-generated.

Incorporating D-amino acids into peptides, or using heterochiral peptides, dramatically increases the diversity of disulfide dynamic combinatorial libraries (DCLs). This chirality effect leads to complex cyclic peptide structures, unlike simpler homochiral libraries.

Keywords:
chiralitycysteine‐rich peptidesdynamic combinatorial chemistrymacrocyclessupramolecular

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Area of Science:

  • Biochemistry
  • Peptide Chemistry
  • Supramolecular Chemistry

Background:

  • Naturally occurring peptides predominantly use L-amino acids.
  • Chirality, the 'handedness' of amino acids, significantly influences peptide folding and self-assembly.
  • Disulfide dynamic combinatorial libraries (DCLs) offer a platform to explore molecular diversity.

Purpose of the Study:

  • To investigate the impact of peptide chirality on the formation and diversity of disulfide DCLs.
  • To compare DCLs generated from heterochiral versus homochiral cysteine-rich peptides.
  • To analyze the structural complexity and isomerism within these DCLs.

Main Methods:

  • Synthesis of short cysteine-rich peptides with varying chirality (L- and D-amino acids).
  • Formation of disulfide DCLs under specific reaction conditions.
  • Analysis of library composition using techniques like mass spectrometry (implied).
  • Characterization of cyclic peptide species and their isomers.

Main Results:

  • Heterochiral tripeptides yield significantly more diverse DCLs compared to homochiral peptides.
  • The most complex library contained numerous cyclic species up to 19-mers.
  • One heterochiral library was estimated to contain 2,045 distinct cyclic compounds, including parallel and antiparallel isomers.
  • Homochiral peptide libraries predominantly formed simple dimers.

Conclusions:

  • Peptide chirality is a critical factor that can be leveraged to dramatically amplify molecular diversity in DCLs.
  • Small changes in amino acid chirality lead to substantial increases in the complexity of self-assembled cyclic peptide structures.
  • This work highlights the potential of using chiral building blocks for designing complex molecular systems.