Enantioseparation of phenylalanine analogs on a quinine-based anion-exchanger chiral stationary phase: Structure and temperature effects

Roland Török, R. Berkecz, A. Péter

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7 Citations (Scopus)

Abstract

Application of a cinchona alkaloid-based chiral anion-exchanger stationary phase for the direct high-performance liquid chromatographic enantioseparation of N-protected unusual phenylalanine analogs is reported. The N-benzyloxycarbonyl, N-3,5-dinitrobenzyloxycarbonyl, N-benzoyl and N-3,5-dinitrobenzoyl derivatives were well separable with high resolution. To achieve optimal separation of the enantiomers, the chromatographic conditions and temperature were varied. Linear van't Hoff plots were observed in the studied temperature range, 278-343 K, and the apparent changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and Gibbs free energy, Δ(ΔG°), were calculated. The values of the thermodynamic parameters depended on the nature of the N-acyl groups, on the structures of the compounds, and especially on the nature of the substituent on C3 of phenylalanine.

Original languageEnglish
Pages (from-to)2523-2532
Number of pages10
JournalJournal of Separation Science
Volume29
Issue number16
DOIs
Publication statusPublished - Nov 2006

Fingerprint

Quinine
Ion exchangers
Phase structure
Phenylalanine
Thermal effects
Anions
Negative ions
Cinchona Alkaloids
Temperature
Enantiomers
Entropy
Gibbs free energy
Thermodynamics
Enthalpy
Derivatives
Liquids

Keywords

  • Chinchona alkaloid-based stationary phase
  • Direct enantiometric separation
  • Phenylalanine analogs
  • Temperature effect

ASJC Scopus subject areas

  • Molecular Medicine
  • Clinical Biochemistry
  • Chemical Engineering(all)
  • Filtration and Separation

Cite this

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title = "Enantioseparation of phenylalanine analogs on a quinine-based anion-exchanger chiral stationary phase: Structure and temperature effects",
abstract = "Application of a cinchona alkaloid-based chiral anion-exchanger stationary phase for the direct high-performance liquid chromatographic enantioseparation of N-protected unusual phenylalanine analogs is reported. The N-benzyloxycarbonyl, N-3,5-dinitrobenzyloxycarbonyl, N-benzoyl and N-3,5-dinitrobenzoyl derivatives were well separable with high resolution. To achieve optimal separation of the enantiomers, the chromatographic conditions and temperature were varied. Linear van't Hoff plots were observed in the studied temperature range, 278-343 K, and the apparent changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and Gibbs free energy, Δ(ΔG°), were calculated. The values of the thermodynamic parameters depended on the nature of the N-acyl groups, on the structures of the compounds, and especially on the nature of the substituent on C3 of phenylalanine.",
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AU - Török, Roland

AU - Berkecz, R.

AU - Péter, A.

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N2 - Application of a cinchona alkaloid-based chiral anion-exchanger stationary phase for the direct high-performance liquid chromatographic enantioseparation of N-protected unusual phenylalanine analogs is reported. The N-benzyloxycarbonyl, N-3,5-dinitrobenzyloxycarbonyl, N-benzoyl and N-3,5-dinitrobenzoyl derivatives were well separable with high resolution. To achieve optimal separation of the enantiomers, the chromatographic conditions and temperature were varied. Linear van't Hoff plots were observed in the studied temperature range, 278-343 K, and the apparent changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and Gibbs free energy, Δ(ΔG°), were calculated. The values of the thermodynamic parameters depended on the nature of the N-acyl groups, on the structures of the compounds, and especially on the nature of the substituent on C3 of phenylalanine.

AB - Application of a cinchona alkaloid-based chiral anion-exchanger stationary phase for the direct high-performance liquid chromatographic enantioseparation of N-protected unusual phenylalanine analogs is reported. The N-benzyloxycarbonyl, N-3,5-dinitrobenzyloxycarbonyl, N-benzoyl and N-3,5-dinitrobenzoyl derivatives were well separable with high resolution. To achieve optimal separation of the enantiomers, the chromatographic conditions and temperature were varied. Linear van't Hoff plots were observed in the studied temperature range, 278-343 K, and the apparent changes in enthalpy, Δ(ΔH°), entropy, Δ(ΔS°), and Gibbs free energy, Δ(ΔG°), were calculated. The values of the thermodynamic parameters depended on the nature of the N-acyl groups, on the structures of the compounds, and especially on the nature of the substituent on C3 of phenylalanine.

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