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Liquid chromatographic enantioseparation of limonene‐based carbocyclic β‐amino acids on zwitterionic Cinchona alkaloid‐based chiral stationary phases
Author(s) -
Lajkó Gyula,
Orosz Tímea,
Ugrai Imre,
Szakonyi Zsolt,
Fülöp Ferenc,
Lindner Wolfgang,
Péter Antal,
Ilisz István
Publication year - 2017
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201700450
Subject(s) - cinchona , chemistry , limonene , chromatography , counterion , alkaloid , organic chemistry , enantiomer , phase (matter) , solvent , amino acid , chiral derivatizing agent , chiral stationary phase , chiral column chromatography , enantioselective synthesis , catalysis , essential oil , ion , biochemistry
The eight stereoisomers of limonene‐based carbocyclic β‐amino acids containing three chiral centers have been directly separated on chiral stationary phases containing Cinchona alkaloid‐based zwitterionic selectors. The effects of bulk solvent composition of the mobile phase, the nature of base additives, counterion concentration, and the structure of selector on the enantiorecognition were studied. Experiments were performed at constant mobile phase composition in the temperature range 5–40°C to study the effect of temperature. Thermodynamic parameters were calculated on the basis of the plots of ln α versus 1/ T curves. The enthalpically or entropically driven enantioseparations were found to depend strongly on the structures of analyte and selector. The eight stereoisomers of limonene‐based carbocyclic β‐amino acids could be differentiated as well‐separated peaks in a traditional 1D chromatographic system in two runs by applying the two complementary ZWIX(+)™ and ZWIX(–)™ columns.