Liquid chromatographic enantioseparation of carbocyclic β-amino acids possessing limonene skeleton on macrocyclic glycopeptide-based chiral stationary phases

Polar-ionic and reversed-phase high-performance liquid chromatographic separations of limonene-based cyclic a-amino acid enantiomers were carried out by using macrocyclic glycopeptide-based chiral selectors applying Chirobiotic T, TAG and R columns. The effects of additives, concentration of the co- and counter-ions and the temperature in polar-ionic mobile phase systems were studied. The influence of pH, MeOH content and alcohol additives were investigated in the reversed-phase mode. The difference in the change in standard enthalpy Delta(Delta H degrees), entropy Delta(Delta S degrees), and free energy Delta(Delta G degrees) was calculated from the linear van't Hoff plots derived from the In a vs la curves in the temperature range 5-40 degrees C. Unusual temperature behavior was observed on Chirobiotic TAG for most of the analytes: decreased retention times were accompanied with increased separation factors with increasing temperature, and separation was entropically-driven. For two of the studied analytes enthalpically-driven enantioseparations were observed. The elution sequence was determined in all cases, but no general rule could be established. (C) 2017 Elsevier B.V. All rights reserved.