Comparison of isothiocyanate chiral derivatizing reagents for high-performance liquid chromatography

M. Péter, F. Fülöp

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

This paper describes the synthesis of a new chiral derivatizing reagent, (1S,2R)-1-acetoxy-1-phenyl-2-propyl isothiocyanate ((S,R)-APPI), which is readily available in both enantiomeric forms after a straightforward two-step synthesis, and compares its separating properties with those of (1S,2S)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate in the indirect high-performance liquid chromatographic separation of the enantiomers of amino compounds. The thiourea diastereomers formed were analysed on a reversed-phase column with methanol as organic mobile-phase modifier. Comparison of the resolution achieved by use of the two reagents revealed that their enantioselectivity might be very different, despite their structural similarity. (S,R)-APPI usually proved to be an excellent chiral derivatizing agent.

Original languageEnglish
Pages (from-to)631-636
Number of pages6
JournalChromatographia
Volume56
Issue number9-10
DOIs
Publication statusPublished - Nov 2002

Keywords

  • Chiral derivatizing reagent
  • Column liquid chromatography
  • Enantioselectivity
  • Indirect enantiomer separation
  • Isothiocyanate

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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