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Related Experiment Videos

Exploring privileged structures: the combinatorial synthesis of cyclic peptides.

Douglas A Horton1, Gregory T Bourne, Mark L Smythe

  • 1Institute for Molecular Bioscience, The University of Queensland, St. Lucia, 4072, Qld., Australia.

Molecular Diversity
|January 29, 2003
PubMed
Summary

Head-to-tail cyclic peptides are privileged structures due to their high affinity for diverse receptors. This review covers their synthesis in combinatorial libraries and biological applications.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Head-to-tail cyclic peptides exhibit high affinity for multiple, unrelated receptor classes.
  • This characteristic suggests they are 'privileged structures' in drug discovery.
  • Cyclic dipeptides (diketopiperazines) are a related class of molecules.

Purpose of the Study:

  • To review synthetic strategies for combinatorial libraries of macrocyclic cyclic peptides and cyclic dipeptides.
  • To highlight the biological applications of these cyclic peptide structures.
  • To provide justification for classifying these molecules as privileged structures.

Main Methods:

  • Review of literature on synthetic methodologies for cyclic peptides.
  • Compilation of examples of combinatorial library synthesis.

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  • Summary of reported biological activities and applications.

    • Main Results:

    • Various strategies exist for synthesizing macrocyclic cyclic peptides and cyclic dipeptides in combinatorial libraries.
    • These cyclic peptides demonstrate a broad range of biological applications.
    • The versatility in binding and application supports their status as privileged structures.

    Conclusions:

    • Cyclic peptides, including macrocyclic and diketopiperazine forms, are valuable privileged structures.
    • Their synthesis via combinatorial libraries facilitates drug discovery.
    • Diverse biological applications underscore their therapeutic potential.