Chiral high-performance liquid chromatography analysis of alpha-amino acid mixtures using a novel SH reagent--N-R-mandelyl-L-cysteine and traditional enantiomeric thiols for precolumn derivatization

J Chromatogr A. 2007 Dec 14;1175(1):89-95. doi: 10.1016/j.chroma.2007.10.034. Epub 2007 Oct 18.

Abstract

Several chiral thiols, i.e. traditionally used enantiomerically pure SH reagents and novel N-R-mandelyl-L-cysteine (R-NMC) containing additional chiral center, have been applied as co-reagents in precolumn derivatization with o-phthalaldehyde for enantiomeric HPLC analysis of individual alpha-amino acids and their mixtures. The R-NMC-derived isoindoles as well as adducts with other thiols have a characteristic absorption maximum at 340 nm, and are highly fluorescent allowing detection of 10 microg/l of an amino acid. Investigated 19 amino acids were analyzed separately and in a mixture by a gradient HPLC after precolumn derivatization. The chromatographic behavior of formed isoindoles substantially differs for each of the thiols used for modification. In contrast to traditional enantiomeric thiols application of diastereomeric R-NMC provides higher resolution for alpha-amino acid enantiomers, with L,D-elution order (except for Arg). Combined use of R-NMC and other thiol enlarges the possibilities of this method, allowing accurate chiral analysis of complex amino acid mixtures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcysteine / chemistry
  • Amino Acids / analysis*
  • Amino Acids / chemistry
  • Chromatography, High Pressure Liquid
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry
  • Indoles / analysis
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Sulfhydryl Reagents / chemistry*
  • o-Phthalaldehyde / chemistry

Substances

  • Amino Acids
  • Indoles
  • N-(R)-mandelyl-(S)-cysteine
  • Sulfhydryl Compounds
  • Sulfhydryl Reagents
  • o-Phthalaldehyde
  • Cysteine
  • Acetylcysteine