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General inverse solid-phase synthesis method for C-terminally modified peptide mimetics.

Ramakrishna Sasubilli1, William G Gutheil

  • 1Division of Pharmaceutical Sciences, School of Pharmacy, University of Missouri-Kansas City, Kansas City, Missouri 64110, USA.

Journal of Combinatorial Chemistry
|November 9, 2004
PubMed
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A new urethane attachment strategy enables versatile synthesis of C-terminally modified peptide mimetics. This method facilitates the creation of diverse peptide mimetic classes for drug discovery and screening.

Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Biotechnology

Background:

  • Peptide mimetics are crucial as bioactive agents and potential drugs.
  • C-terminally modified peptide mimetics offer significant synthetic advantages due to carboxyl group versatility.

Purpose of the Study:

  • To describe a general approach for synthesizing C-terminally modified peptide mimetics.
  • To demonstrate the utility of this approach for creating diverse peptide mimetic classes.

Main Methods:

  • A urethane attachment strategy combined with N-to-C peptide synthesis using amino acid t-butyl esters.
  • Application of the method for solid-phase synthesis of peptide trifluoromethyl ketones, boronic acids, and hydroxamic acids.

Main Results:

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  • A versatile and general synthetic approach for C-terminally modified peptide mimetics was developed.
  • The method is compatible with standard solution-phase peptide mimetic synthesis conditions.
  • Demonstrated solid-phase synthesis of peptide trifluoromethyl ketones, boronic acids, and hydroxamic acids.

Conclusions:

  • The developed approach provides a foundation for combinatorial and parallel solid-phase synthesis of peptide mimetics.
  • This facilitates bioactive agent screening and further development of C-terminal functional group strategies.