High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids

Lajkó, Gyula; Orosz, Tímea; Grecsó, Nóra; Fekete, Beáta; Palkó, Márta; Fülöp, Ferenc; Lindner, Wolfgang; Péter, Antal; Ilisz, István

doi:10.1016/j.aca.2016.03.044

Cited by 22 publications

(17 citation statements)

References 42 publications

(54 reference statements)

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“…The slopes of the log k versus log c plots in this study (0.25–0.31) are in accordance with our results obtained on ZWIX phases working in zwitterionic mode . However, ZWIX phases working in a “uni‐ionic” mode as anion‐exchanger or cation‐exchanger exhibited steeper slopes (0.6–1.0). These values indicate a marked difference between the concerted zwitterionic and a “uni‐ionic” ion‐exchange mechanism.…”

Section: Resultssupporting

confidence: 91%

Liquid chromatographic enantioseparation of limonene‐based carbocyclic β‐amino acids on zwitterionic Cinchona alkaloid‐based chiral stationary phases

Lajkó

Orosz

Ugrai

et al. 2017

J of Separation Science

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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.

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Section: Resultssupporting

confidence: 91%

Liquid chromatographic enantioseparation of limonene‐based carbocyclic β‐amino acids on zwitterionic Cinchona alkaloid‐based chiral stationary phases

Lajkó

Orosz

Ugrai

et al. 2017

J of Separation Science

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“…The influence of water applied in lower percentages (≤10 v%) was studied in additional cases [53,84,95,106,107,116]. The presence of water in the eluent turned out to be favorable on the separation factor of peptides with lipophilic residues [116], while no beneficial effect of the water addition (1-5 v%) was observed for the enantioseparation of highly polar aminophosphonic acids [84].…”

Section: Effect Of Bulk Phase Modifiersmentioning

confidence: 99%

“…Employing hydro-organic eluent systems (MeOH and/or ACN and water) for the enantioresolution of primary ß-amino acids the best separations were achieved with ACN as bulk solvent containing not more than 10 v% water [106]. In the case of ß-aminohydroxamic acids, introduction of water into the MeOH/ACN mobile phase system in increasing amounts led to a marked reduction in retention times followed by a continuous decrease in selectivity [107].…”

Section: Effect Of Bulk Phase Modifiersmentioning

confidence: 99%

Liquid chromatographic enantiomer separations applying chiral ion-exchangers based on Cinchona alkaloids

Ilisz

Bajtai

Lindner

et al. 2018

Journal of Pharmaceutical and Biomedical Analysis

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“…The relative contribution of enthalpic and entropic terms to the free energy of adsorption can be visualized through the enthalpy/entropy ratio Q. 45,46 Comparison of Q values revealed that the enantioseparation was mainly enthalpically controlled in most cases as reflected by Q larger than 1 values. Interestingly, enthropy controlled enantioseparations (Q < 1) were observed using Chiralpak AD as stationary phase and IPA or ACN as mobile phase.…”

Section: Effect Of Column Temperature On Chiral Separation Of Rac mentioning

confidence: 99%

Enantioseparation of racecadotril using polysaccharide‐type chiral stationary phases in polar organic mode

et al. 2017

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Enantioseparation of the antidiarrheal drug, racecadotril, was investigated by liquid chromatography using polysaccharide-type chiral stationary phases in polar organic mode. The enantiodiscrimininating properties of 4 different chiral columns (Chiralpak AD, Chiralcel OD, Chiralpak AS, Chiralcel OJ) with 5 different solvents (methanol, ethanol, 1-propanol, 2-propanol, and acetonitrile) at 5 different temperatures (5-40°C) were investigated. Apart from Chiralpak AS column the other 3 columns showed significant enantioseparation capabilities.Among the tested mobile phases, alcohol type solvents were superior over acetonitrile, and significant differences in enantioselective performance of the selector were observed depending on the type of alcohol employed. Van't Hoff analysis was used for calculation of thermodynamic parameters which revealed that enantioseparation is mainly enthalpy controlled; however, enthropic control was also observed. Enantiopure standard was used to determine the enantiomer elution order, revealing chiral selector-and mobile-phase dependent reversal of enantiomer elution order. Using the optimized method (Chiralcel OJ stationary phase, thermostated at 10°C, 100% methanol, flow rate: 0.6 mL/min) baseline separation of racecadotril enantiomers (resolution = 3.00 ± 0.02) was achieved, with the R-enantiomer eluting first. The method was validated according to the ICH guidelines, and its application was tested on capsule and granules containing the racemic mixture of the drug.

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High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids

Cited by 22 publications

References 42 publications

Liquid chromatographic enantioseparation of limonene‐based carbocyclic β‐amino acids on zwitterionic Cinchona alkaloid‐based chiral stationary phases

Liquid chromatographic enantioseparation of limonene‐based carbocyclic β‐amino acids on zwitterionic Cinchona alkaloid‐based chiral stationary phases

Liquid chromatographic enantiomer separations applying chiral ion-exchangers based on Cinchona alkaloids

Enantioseparation of racecadotril using polysaccharide‐type chiral stationary phases in polar organic mode

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