Development of the high-performance liquid chromatographic method for the enantioseparation of unusual glycine ester analogs on polysaccharide-based chiral stationary phases

Anita Aranyi, István Ilisz, Nóra Grecsó, Renáta Csütörtöki, István Szatmári, Ferenc Fülöp, Antal Péter

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The stereoisomers of ten unusual amino acid analogs, 1- and 2-naphthol-substituted glycine and its ester derivatives, were separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-1), cellulose tris-(3-chloro-4-methylphenylcarbamate) (Cellulose-2), cellulose tris-(4-methylbenzoate) (Cellulose-3), cellulose tris-(4-chloro-3-methylphenylcarbamate) (Cellulose-4) and amylose tris-(5-chloro-2-methylphenylcarbamate) (Amylose-2). Experiments were performed in normal-phase mode with n-heptane/alcohol/diethylamine mobile phases in a wide temperature range: 5-50°C. Thermodynamic parameters were calculated from plots of lnk or lnα vs. 1/T. Δ(ΔH°) ranged from -10.1 to 6.2kJmol-1, Δ(ΔS°) from -31.5 to 22.5Jmol-1K-1 and -Δ(ΔG°) from 0.4 to 1.4kJmol-1, and both enthalpy and entropy-controlled enantioseparations were observed. The latter was advantageous with regard to the shorter retention and greater selectivity at high temperature. The sequence of elution of the stereoisomers was determined in some cases.

Original languageEnglish
Pages (from-to)183-191
Number of pages9
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume76
DOIs
Publication statusPublished - Mar 25 2013

Keywords

  • Column liquid chromatography
  • Enantiomer separation
  • Gly analogs
  • Lux Amylose-2 column
  • Lux Cellulose columns

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

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