Regioselective formation, using orthogonal cysteine protection, of an alpha-conotoxin dimer peptide containing four disulfide bonds

Org Lett. 2003 Aug 7;5(16):2955-7. doi: 10.1021/ol035105w.

Abstract

[structure: see text] The combination of the cysteine thiol protecting groups Trt, Acm, tBu, and MeBzl were used for the regioselective formation of an alpha-conotoxin dimer peptide containing four disulfide bridges. Additionally, a protocol is described whereby two one-pot oxidations were employed in order to improve the efficiency of the folding process. The target compound was produced in good yield.

MeSH terms

  • Amino Acid Sequence
  • Chromatography, High Pressure Liquid
  • Conotoxins / chemistry*
  • Cysteine / chemistry*
  • Dimerization
  • Disulfides / chemistry*
  • Molecular Sequence Data
  • Oxidation-Reduction

Substances

  • Conotoxins
  • Disulfides
  • Cysteine