Application of (1S,2S)- and (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2- propylisothiocyanate to the indirect enantioseparation of racemic proteinogenic amino acids

M. Péter, A. Péter, F. Fülöp

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The application of (1S,2S)- or (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)- 2-propylisothiocyanate as a new chiral derivatizing agent for the resolution of compounds possessing an amino group is described. The reagent is easily accessible in both enantiomeric forms after a simple two-step synthesis. Its applicability was demonstrated on the example of the resolution of a series of α-amino acids. The diastereomeric thiourea derivatives produced were separated by reversed-phase high-performance liquid chromatography. The effects of pH, temperature and reagent excess on the derivatization kinetics were investigated, as were the effects of pH and organic modifier on the separation. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)115-126
Number of pages12
JournalJournal of Chromatography A
Volume871
Issue number1-2
DOIs
Publication statusPublished - Feb 25 2000

Keywords

  • Amino acids
  • Derivatization, LC
  • Diacetoxynitrophenylpropylisothiocyanate
  • Enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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