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Dynamic cyclic thiodepsipeptide libraries from thiol-thioester exchange.

Soumyadip Ghosh1, Lindsey A Ingerman, Aaron G Frye

  • 1Department of Chemistry, CB 3290, University of North Carolina, Chapel Hill, North Carolina 27599, USA.

Organic Letters
|March 25, 2010
PubMed
Summary
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Dynamic combinatorial chemistry assays can now utilize libraries of cyclic thiodepsipeptides, generated through efficient thiol-thioester exchange under thermodynamic control. This method explores macrocycle formation kinetics and amino acid influences.

Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Medicinal Chemistry

Background:

  • Cyclic thiodepsipeptides are valuable scaffolds in drug discovery.
  • Dynamic combinatorial chemistry (DCC) offers a powerful approach for generating molecular diversity.
  • Efficient methods for constructing cyclic thiodepsipeptide libraries are needed for DCC applications.

Purpose of the Study:

  • To develop a robust method for generating libraries of cyclic thiodepsipeptides.
  • To investigate the thermodynamic and kinetic aspects of macrocycle formation.
  • To enable the application of these libraries in dynamic combinatorial chemistry assays.

Main Methods:

  • Thiol-thioester exchange reactions.
  • Thermodynamic control of macrocyclization.

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  • Kinetic analysis of reaction pathways.
  • Exploration of diverse amino acid building blocks.

    • Main Results:

    • Readily generated libraries of cyclic thiodepsipeptides.
    • Achieved macrocycle formation under thermodynamic control.
    • Identified kinetic determinants governing macrocyclization.
    • Demonstrated the influence of amino acid structure on reaction dynamics.

    Conclusions:

    • Thiol-thioester exchange is an effective strategy for creating cyclic thiodepsipeptide libraries for DCC.
    • Understanding reaction kinetics and substrate structure is crucial for optimizing macrocycle formation.
    • This methodology expands the toolkit for synthesizing complex cyclic peptides.