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Analytical Tools for Dynamic Combinatorial Libraries of Cyclic Peptides.

Taleen Peker1, Benjamin Zagiel1, Lou Rocard1

  • 1Sorbonne Université, École Normale Supérieure, PSL University, CNRS, Laboratoire des Biomolécules, LBM, 75005, Paris, France.

Chembiochem : a European Journal of Chemical Biology
|October 10, 2023
PubMed
Summary

This study introduces new analytical tools for characterizing dynamic combinatorial peptide libraries, overcoming previous limitations and enabling the discovery of bioactive peptides.

Keywords:
cyclic peptidedynamic combinatorial chemistrymass spectrometrythioester exchange

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Area of Science:

  • Medicinal Chemistry
  • Analytical Chemistry
  • Biochemistry

Background:

  • Dynamic combinatorial chemistry (DCC) is promising for discovering bioactive peptides.
  • Previous DCC applications were limited by analytical challenges with diverse peptide libraries.
  • Thiol-to-thioester exchange enables generating large, dynamic cyclic peptide libraries under biocompatible conditions.

Purpose of the Study:

  • To develop analytical tools for characterizing dynamic combinatorial libraries of cyclic peptides.
  • To simplify the distinction of isomers within these libraries.
  • To facilitate the discovery of novel bioactive peptides using DCC.

Main Methods:

  • High-Performance Liquid Chromatography (HPLC) for library separation.
  • Mass Spectrometry (MS) for molecular identification.
  • MS/MS fragmentation analysis for isomer sequencing and structural elucidation.

Main Results:

  • Developed HPLC and MS methods for efficient characterization of complex peptide libraries.
  • Simplified isomer distinction through targeted MS/MS fragmentation.
  • Identified a UV-tag (415 nm) and ornithine residue that facilitate regioselective fragmentation.

Conclusions:

  • The presented analytical tools overcome key challenges in characterizing dynamic combinatorial peptide libraries.
  • This advancement enables the application of DCC for the discovery of bioactive cyclic peptides.
  • Optimized cyclic peptide scaffolds with specific features enhance analytical tractability and drug discovery potential.