Reversed-Phase Liquid Chromatographic Separation, on Cellulose Chiral Stationary Phases, of the Stereoisomers of Methoxytetra-hydronaphthalene Derivatives, New Agonist and Antagonist Ligands for Melatonin Receptors

Lipka, Emmanuelle; Descamps, C.; Vaccher, Claude; Bonte, Jean‐Paul

doi:10.1365/s10337-004-0491-6

Cited by 10 publications

(9 citation statements)

References 26 publications

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“…Their chiral recognition abilities depend on the property, position, and number of substituents, and generally, the introduction of an electron-donating methyl group or an electron-withdrawing halogen at the 3-and/ or 4-position of the phenyl ring improves the chiral recognition ability for many racemates [24]. Hydrophobicity, electrostatic interaction, p -p interaction, hydrogen bonding, dipole -dipole interaction, and steric hindrance seem to be of major importance in enantioseparation mechanisms [25].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Qin

Wang

et al. 2007

J of Separation Science

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Twenty chiral pesticides were tested, of which seven samples were directly separated by HPLC using cellulose tris-3,5-dimethyl carbamate (CDMPC) chiral stationary phase under RP conditions. The influence of mobile phase composition and column temperatures from 0 degrees C to 40 degrees C on the separations were investigated. The mobile phases were methanol/water or ACN/water at a flow rate of 0.8 mL/min with UV detection at 230 or 210 nm. Epoxiconazole, terallethrin, benalaxyl, and diclofopmethyl were observed to obtain the baseline separation under suitable conditions and other pesticides pyriproxyfen, lactofen, and quizalofop-ethyl were separated partially. The retention factors (k) and selectivity factor (alpha) for the enantiomers of most investigated pesticides decreased upon increasing the temperature except for the selectivity factors (alpha) of pyriproxyfen in methanol/water. The ln alpha - 1/T plots for racemic chiral pesticides were linear at the range of 0-40 except for that of pyriproxyfen enantiomers in methanol/water and the chiral separations were controlled by enthalpy. Better separations were not always at low temperature. The elution orders of the eluting enantiomers were determined by a circular dichroism (CD) detector.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Qin

Wang

et al. 2007

J of Separation Science

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“…Many chiral separations have been studied on polysaccharide CSPs and satisfactory mechanisms have been proposed. It is generally considered that some evocable reaction between the chiral stationary phase and the enantiomers such as hydrogen, π–π, and dipole–dipole interactions contribute to the successful enantiomer separation by polysaccharide CSPs . The cavity (produced by a single‐handed helical structure of polysaccharide formed by the glucose unit of CSPs) inside CSPs and the spatial adaptability of the solute also have important impacts on the stereoselectivity .…”

Section: Resultsmentioning

confidence: 99%

“…It is generally considered that some evocable reaction between the chiral stationary phase and the enantiomers such as hydrogen, π-π, and dipole-dipole interactions contribute to the successful enantiomer separation by polysaccharide CSPs. 20 The cavity (produced by a single-handed helical structure of polysaccharide formed by the glucose unit of CSPs) inside CSPs and the spatial adaptability of the solute also have important impacts on the stereoselectivity. 21 Comprehensive effects of several interactions influenced the stabilities of the instantaneous diastereomeric complexes of chiral stationary phase and enantiomers and made a difference so that the enantiomers could be separated.…”

Section: Chiral Separations Under Reverse Phasementioning

confidence: 99%

Enantiomeric Separations of Pyriproxyfen and its Six Chiral Metabolites by High‐Performance Liquid Chromatography

et al. 2016

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Pyriproxyfen is a chiral insecticide, and over 10 metabolites have been identified in the environment. In this work the separations of the enantiomers of pyriproxyfen and its six chiral metabolites were studied by high-performance liquid chromatography (HPLC). Both normal phase and reverse phase were applied using the chiral columns Chiralpak IA, Chiralpak IB, Chiralpak IC, Chiralcel OD, Chiralcel OD-RH, Chiralpak AY-H, Chiralpak AD-H, Chiracel OJ-H, (R,R)-Whelk-O 1, and Lux Cellulose-3. The effects of the chromatographic parameters such as mobile phase composition and temperature on the separations were investigated and the enantiomers were identified with an optical rotation detector. The enantiomers of these targets could obtain complete separations (resolution factor Rs > 1.5) on Chiralpak IA, Chiralpak IB, Chiralcel OD, Chiralpak AY-H, or Chiracel OJ-H under normal conditions. Chiralcel OJ-H showed the best chiral separation results with n-hexane as mobile phase and isopropanol (IPA) as modifier. The simultaneous enantiomeric separation of pyriproxyfen and four chiral metabolites was achieved on Chiralcel OJ-H under optimized condition: n-hexane/isopropanol = 80/20, 15°C, flow rate of 0.8 ml/min, and UV detection at 230 nm. The enantiomers of pyriproxyfen and the metabolites , , and obtained complete separations on Chiralpak IA, Chiralpak IC, and Lux Cellulose-3 under reverse phase using acetonitrile/water as the mobile phase. The retention factors (k) and selectivity factors (α) decreased with increasing temperature, and the separations were better under low temperature in most cases. The work is of significance for the investigation of the environmental behaviors of pyriproxyfen on an enantiomeric level.

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“…In reversed‐phase HPLC, the influence of organic solvent volume fraction ( ϕ ) in mobile phase on retention and selectivity might be described using some dependences []. Methanolic mobile phase exhibited less elution strength and low efficiency compared to acetonitrile [] and gave poor chiral recognition ( k (S‐AMB) = 26.3; R = 1.31 and N = 385 for ϕ = 0.5). On the other hand, good chiral recognition was achieved using propan‐2‐ol but the substantial loss of efficiency was observed ( k (S‐AMB) = 3.79; R = 2.04 and N = 1445 for ϕ = 0.4).…”

Section: Resultsmentioning

confidence: 99%

Rapid determination of ambrisentan enantiomers by enantioselective liquid chromatography using cellulose‐based chiral stationary phase in reverse phase mode

Douša¹,

Gibala²

2012

J of Separation Science

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A sensitive, specific, and rapid high-performance liquid chromatography (HPLC) method for the determination of ambrisentan enantiomers has been developed and validated. Six chiral columns were tested in a reversed-phase system. Excellent enantioseparation with the resolution more than 2.5 was achieved on Chiralcel OZ-3R (cellulose 3-chloro-4-methylphenylcarbamate) using mixture of 20 mM sodium formate (pH 3.0) with acetonitrile (55:45; v/v). Validation of the HPLC method including linearity, limit of detection, limit of quantification, precision, accuracy, and selectivity was performed according to the International Conference on Harmonisation (ICH) guidelines. The method has an advantage of a very quick chromatographic separation (less than 6 min) and therefore is highly suitable for routine determination of (R)-ambrisentan in enantiopure active pharmaceutical ingredient (S)-ambrisentan.

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Reversed-Phase Liquid Chromatographic Separation, on Cellulose Chiral Stationary Phases, of the Stereoisomers of Methoxytetra-hydronaphthalene Derivatives, New Agonist and Antagonist Ligands for Melatonin Receptors

Cited by 10 publications

References 26 publications

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Enantiomeric separation of chiral pesticides by high performance liquid chromatography on cellulose tris‐3,5‐dimethyl carbamate stationary phase under reversed phase conditions

Enantiomeric Separations of Pyriproxyfen and its Six Chiral Metabolites by High‐Performance Liquid Chromatography

Rapid determination of ambrisentan enantiomers by enantioselective liquid chromatography using cellulose‐based chiral stationary phase in reverse phase mode

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