Configuration and racemization determination of cysteine residues in peptides by chiral derivatization and HPLC: application to oxytocin peptides

J Pept Sci. 2001 Jun;7(6):316-22. doi: 10.1002/psc.325.

Abstract

An improved RP-HPLC method was developed for the determination of the configuration and stereochemical purity of cysteine residues in peptides. The method consists of oxidation of cysteine and cystine residues to cysteic acid, followed by hydrolysis and pre-column chiral derivatization with Val-Marfey's reagent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid / methods*
  • Cysteic Acid / analysis
  • Cysteic Acid / chemistry
  • Cysteine / analysis*
  • Cysteine / chemistry*
  • Fluorescence
  • Hydrolysis
  • Isomerism
  • Molecular Conformation
  • Oxidants / metabolism
  • Oxytocin / analogs & derivatives
  • Oxytocin / chemical synthesis
  • Oxytocin / chemistry*
  • Peptide Fragments / chemical synthesis
  • Peptide Fragments / chemistry*
  • o-Phthalaldehyde / chemistry

Substances

  • Oxidants
  • Peptide Fragments
  • Oxytocin
  • o-Phthalaldehyde
  • Cysteic Acid
  • Cysteine