Determination of the absolute configuration of selenomethionine from antarctic krill by RP-HPLC/ICP-MS using chiral derivatization agents

Anal Bioanal Chem. 2004 Mar;378(6):1624-9. doi: 10.1007/s00216-003-2472-2.

Abstract

A fast and sensitive method was developed for the determination of the absolute configuration of selenomethionine. The enantiomers of selenomethionine were converted into diastereomeric isoindole derivatives by reaction with o-phthaldialdehyde and N-isobutyryl-L-cysteine. This easy-to-handle reaction proceeds quantitatively in a few minutes at room temperature. Separation and detection of the diastereomers was achieved by reversed-phase high-performance liquid chromatography-inductively coupled plasma-mass spectrometry (RP-HPLC/ICP-MS) using a conventional C18 reversed-phase column. Detection limits of about 4 microg L(-1) were obtained. The method was applied to the determination of the configuration of selenomethionine extracted from antarctic krill, which turned out to possess the L-configuration.

MeSH terms

  • Animals
  • Antarctic Regions
  • Chromatography, High Pressure Liquid / methods
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry*
  • Euphausiacea / chemistry*
  • Indoles / chemistry
  • Mass Spectrometry / methods
  • Molecular Structure
  • Selenomethionine / analysis*
  • Selenomethionine / chemistry*
  • Stereoisomerism
  • o-Phthalaldehyde / chemistry*

Substances

  • Indoles
  • N-isobutyrylcysteine
  • o-Phthalaldehyde
  • Selenomethionine
  • Cysteine