Facile preparation of disulfide-bridged peptides using the polymer-supported oxidant CLEAR-OX™

K. Darlak, D. Wiegandt Long, A. Czerwinski, M. Darlak, F. Valenzuela, A. F. Spatola, G. Barany

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

Formation of disulfide bonds in synthetic peptides is one of the more challenging transformations to achieve in peptide chemistry, in view of the possible formation of oligomeric by-products and other side reactions, as well as occasional solubility problems in aqueous oxidizing media. It was shown previously that 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB ≡ Ellman's reagent), when attached to polyethylene glycol-polystyrene (PEG-PS™), controlled-pore glass (CPG), or modified Sephadex supports, was an effective oxidizing agent that promoted disulfide formation under mild conditions. More recently, this work was extended to Cross-Linked Ethoxylate Acrylate Resin (CLEAR) supports, because of their compatibility with both organic and aqueous solvent mixtures. The resultant new tool, termed CLEAR-OX™, was used to conveniently produce several model cyclic disulfides with improved purities and yields, when compared with solution oxidations. A particularly striking example was the gram-scale oxidation of a urotensin II antagonist peptide containing a hindered penicillamine unit.

Original languageEnglish (US)
Pages (from-to)303-312
Number of pages10
JournalJournal of Peptide Research
Volume63
Issue number3
DOIs
StatePublished - Mar 2004

Keywords

  • Cross-Linked Ethoxylate Acrylate Resin supports
  • Disulfide-bridged peptides
  • Ellman's reagent
  • Oxidation
  • Penicillamine-containing sequences
  • Polymer-bound oxidant
  • Potassium ferricyanide
  • Solid-phase Ellman's reagent
  • Urotensin II antagonist

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