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Related Experiment Videos

Cyclization of disulfide-containing peptides in solid-phase synthesis.

F Albericio1, R P Hammer, C García-Echeverría

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

International Journal of Peptide and Protein Research
|May 1, 1991
PubMed
Summary

Solid-phase synthesis enables high yields of disulfide-containing peptides by leveraging pseudo-dilution for intramolecular cyclization. This method efficiently produces complex cyclic peptides with preserved disulfide bonds.

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Area of Science:

  • Peptide Chemistry
  • Solid-Phase Synthesis
  • Bioconjugation

Background:

  • Disulfide bonds are crucial for peptide structure and function.
  • Traditional solution-phase synthesis of cyclic peptides with disulfide bonds can be challenging due to aggregation and low yields.

Purpose of the Study:

  • To develop an efficient solid-phase synthesis method for producing disulfide-containing peptides.
  • To utilize the pseudo-dilution effect on solid supports to favor intramolecular disulfide bond formation.

Main Methods:

  • Peptide synthesis on polymeric supports using Boc and Fmoc protection strategies.
  • Employing various protecting groups for cysteine/penicillamine beta-thiols (Acm, Fm, Trt).
  • Utilizing diverse resin linkages (MBHA, PAL, Nonb) and oxidation methods on-resin.

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Main Results:

  • Successful synthesis and oxidation of model peptides (Ac-Cys-Pro-DVal-Cys-NH2, Ac-Pen-Pro-DVal-Cys-NH2) and oxytocin.
  • High yields (60-90%) of disulfide-containing peptides obtained.
  • Preservation of disulfide bridges during cleavage from the solid support.

Conclusions:

  • Solid-phase synthesis offers a robust and efficient approach for constructing disulfide-containing peptides.
  • The pseudo-dilution phenomenon on solid supports significantly enhances intramolecular cyclization.
  • This methodology provides a versatile platform for synthesizing complex cyclic peptides.