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

M. Péter, F. Fülöp

Research output: Article

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
Publication statusPublished - nov. 2002

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High performance liquid chromatography
High Pressure Liquid Chromatography
Thiourea
Enantiomers
Enantioselectivity
Methanol
Liquids
isothiocyanic acid
4-nitrophenyl

ASJC Scopus subject areas

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

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title = "Comparison of isothiocyanate chiral derivatizing reagents for high-performance liquid chromatography",
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.",
keywords = "Chiral derivatizing reagent, Column liquid chromatography, Enantioselectivity, Indirect enantiomer separation, Isothiocyanate",
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AU - Péter, M.

AU - Fülöp, F.

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N2 - 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.

AB - 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.

KW - Chiral derivatizing reagent

KW - Column liquid chromatography

KW - Enantioselectivity

KW - Indirect enantiomer separation

KW - Isothiocyanate

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