N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis

Org Lett. 2013 Feb 1;15(3):616-9. doi: 10.1021/ol303428d. Epub 2013 Jan 15.

Abstract

N-Chlorosuccinimide is described as a widely applicable on-resin disulfide-forming reagent. Disulfide bond formation was completed within 15 min in DMF. This strategy was successfully used in the synthesis of oxytocin and a regioselective synthesis of an α-conotoxin. Moreover, disulfide formation with N-chlorosuccinimide was found to be compatible with oxidation-prone methionine and tryptophan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Conotoxins / chemical synthesis
  • Disulfides / chemistry*
  • Indicators and Reagents
  • Methionine / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Polymers / chemistry
  • Solid-Phase Synthesis Techniques
  • Succinimides / chemistry*
  • Tryptophan / chemistry

Substances

  • Conotoxins
  • Disulfides
  • Indicators and Reagents
  • Polymers
  • Succinimides
  • N-chlorosuccinimide
  • Tryptophan
  • Methionine