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

Roland Török, Robert Berkecz, Antal Péter

Research output: Article

8 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. 1 2006

ASJC Scopus subject areas

  • Analytical Chemistry
  • Filtration and Separation

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