High-performance liquid chromatographic separation of unusual amino acid enantiomers derivatized with (1S,2S)-1,3-diacetoxy-1-(4-nitrophenyl)-2- propyl-isothiocyanate

A. Péter, M. Péter, F. Fülöp, G. Török, G. Tóth, D. Tourwé, J. Sápi

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Abstract

A new chiral derivatizing agent (CDA), (1S,2S)-1,3-diacetoxy-1-(4- nitrophenyl)-2-propylisothiocyanate, (S,S)-DANI, was applied to the separation of the enantiomers of unusual amino acids containing two chiral centers. Different β-methyl-α-amino acids (β-MePhe, β-MeTyr and β-MeTrp) and β-amino acids with cycloalkane skeletons (2-aminocyclopentanecarboxylic acid and 2-aminocyclohexanecarboxylic acid) were derivatized and the thiourea derivatives produced were separated by reversed-phase high-performance liquid chromatography. The applicability of this new CDA in the separation of unusual amino acids is demonstrated. The four stereoisomers of the investigated amino acids (except β-MePhe) could be separated in one chromatographic run.

Original languageEnglish
Pages (from-to)S148-S154
JournalChromatographia
Volume51
Issue number1
Publication statusPublished - Jan 1 2000

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Keywords

  • (1S,2S)-1,3-Diacetoxy-1-(4-nitrophenyl)-2- propyli-sothiocyanate
  • Chiral derivatization
  • Column liquid chromatography
  • Indirect separation
  • Unusual amino acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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