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Disulfide bond formation in peptides

I Annis1, B Hargittai, G Barany

  • 1Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.

Methods in Enzymology
|January 1, 1997
PubMed
Summary

This review explores chemical strategies for creating disulfide bonds in synthetic peptides and proteins. Various oxidation and directed methods offer options for optimizing disulfide bond formation, yielding pure products.

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Area of Science:

  • Peptide and Protein Chemistry
  • Synthetic Organic Chemistry

Background:

  • Disulfide bonds are crucial for the structure and function of many peptides and proteins.
  • Efficient formation of disulfide bonds in synthetic molecules remains a challenge.

Purpose of the Study:

  • To review and present diverse chemical methodologies for synthesizing disulfide bonds in peptides and small proteins.
  • To categorize and compare different approaches for disulfide bond formation.

Main Methods:

  • Oxidation of unprotected thiols.
  • Oxidation of protected thiols.
  • Directed synthesis of unsymmetrical disulfides.
  • Reactions performed in solution or on solid supports.

Main Results:

  • Three primary categories of disulfide bond formation strategies were identified.
  • Product yield and purity are contingent upon protecting group selection, reaction conditions, and target structure.
  • Successful synthesis is achievable through optimization of available methods.

Conclusions:

  • A variety of chemical approaches exist for forming disulfide bonds in synthetic peptides and proteins.
  • The choice of method and optimization of conditions are critical for achieving desired outcomes.
  • Sufficient options are available to facilitate successful disulfide bond formation.

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