A closer study of chiral retention mechanisms

Fornstedt, Torgny; Sajonz, Peter; Guiochon, Georges

doi:10.1002/(sici)1520-636x(1998)10:5<375::aid-chir3>3.0.co;2-5

Cited by 114 publications

(44 citation statements)

References 39 publications

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“…[48][49][50][51][52] Several papers have been published discussing the effects of temperature on enantiomeric HPLC separations. [53][54][55][56][57] The dependence of the retention of an analyte on temperature can be expressed by the van't Hoff equation, which may be interpreted in terms of mechanistic aspects of chiral recognition:…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Separation of Bicyclo[2.2.2]octane‐Based 2‐Amino‐3‐Carboxylic Acids on Macrocyclic Glycopeptide Chiral Stationary Phases

et al. 2014

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Direct high-performance liquid chromatographic (HPLC) separation of four bicyclo[2.2.2]octane based 2-amino-3-carboxylic acid enantiomers were developed on chiral stationary phases (CSPs) containing different macrocyclic glycopeptide antibiotic selectors. The analyses were performed under reversed-phase, polar organic and polar ionic mode on macrocyclic-glycopeptide-based Chirobiotic T, T2, TAG, and R columns. The effects of the mobile phase composition including the acid and base modifier, the structure of the analytes, and the temperature on the separations were investigated. Experiments were achieved at constant mobile phase compositions on different stationary phases in the temperature range 5-40°C. Thermodynamic parameters were calculated from plots of ln k or ln α versus 1/T. It was recognized that the enantioseparations in reversed-phase and polar organic mode were enthalpically driven, but under polar-ionic conditions entropically driven enantioseparation was observed as well. Baseline separation and determination of elution sequence were achieved in all cases.

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Section: Introductionmentioning

confidence: 99%

Enantiomeric Separation of Bicyclo[2.2.2]octane‐Based 2‐Amino‐3‐Carboxylic Acids on Macrocyclic Glycopeptide Chiral Stationary Phases

et al. 2014

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“…The retention mechanism involved in chiral recognition of the CSPs was studied in many works. [2][3][4][5][6][7][8] The "three-point attachment model" was one of the early attempts to rationalize the enantiospecific interactions between enantiomers with the chiral selector. It was hypothesized that the enantiomer that will display the best optimum fit, by the formation of the three interactions, will elute later than the other enantiomer that will be less fitting.…”

Section: Introductionmentioning

confidence: 99%

Predictability of Enantiomeric Chromatographic Behavior on Various Chiral Stationary Phases Using Typical Reversed Phase Modeling Software

et al. 2013

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Pharmaceutical companies worldwide tend to apply chiral chromatographic separation techniques in their mass production strategy rather than asymmetric synthesis. The present work aims to investigate the predictability of chromatographic behavior of enantiomers using DryLab HPLC method development software, which is typically used to predict the effect of changing various chromatographic parameters on resolution in the reversed phase mode. Three different types of chiral stationary phases were tested for predictability: macrocyclic antibiotics-based columns (Chirobiotic V and T), polysaccharide-based chiral column (Chiralpak AD-RH), and protein-based chiral column (Ultron ES-OVM). Preliminary basic runs were implemented, then exported to DryLab after peak tracking was accomplished. Prediction of the effect of % organic mobile phase on separation was possible for separations on Chirobiotic V for several probes: racemic propranolol with 97.80% accuracy; mixture of racemates of propranolol and terbutaline sulphate, as well as, racemates of propranolol and salbutamol sulphate with average 90.46% accuracy for the effect of percent organic mobile phase and average 98.39% for the effect of pH; and racemic warfarin with 93.45% accuracy for the effect of percent organic mobile phase and average 99.64% for the effect of pH. It can be concluded that Chirobiotic V reversed phase retention mechanism follows the solvophobic theory.

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“…Differences in the higher-order structures among cellulose and amylose are also responsible for differences in chiral discrimination. [8][9][10] Due to their broad applicability and to the fact that the use of buffered aqueous mobile phases is compatible with biological fluids, protein-based columns have become very popular. Commercially available columns have been prepared with bovine serum albumin, human serum albumin, cellobiohydrolase, human a-1-acid glycoprotein and ovomucoid proteins.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

Bonato¹,

Bortocan²,

Gaitani³

et al. 2002

J. Braz. Chem. Soc.

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Várias fases estacionárias baseadas em derivados de polissacarídeos e proteínas foram avaliadas para a resolução de alguns fármacos quirais e seus metabólitos. As fases estacionárias baseadas em polissacarídeos CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD e CHIRALPAK AS foram avaliadas em condições de fase normal, usando hexano:2-propanol como fase móvel. Dietilamina ou ácido trifluoracético foram adicionados para melhorar a simetria dos picos. As colunas CHIRALCEL OJ-R, CHIRALCEL OD-R e CHIRALCEL OD-H foram avaliadas em condições de fase reversa, usando acetonitrila:água ou acetonitrila: NaClO 4 . As fases estacionárias baseadas em proteínas CHIRAL AGP e ULTRON ES-OVM foram usadas com fases móveis consistindo de soluções tampão adicionadas de modificadores orgânicos. Entre as fases estacionárias baseadas em derivados de polissacarídeos, a CHIRALPAK AD mostrou melhor resolução de quase todos os fármacos e metabólitos estudados. A coluna ULTRON ES-OVM foi particularmente útil para a resolução dos quatro estereoisômeros da tioridazina-2-sulfóxido.Several chiral stationary phases based on polysaccharide derivatives and proteins were evaluated for the resolution of some chiral drugs and their metabolites. The polysaccharide-based stationary phases CHIRALCEL OD-H, CHIRALCEL OB-H, CHIRALCEL OJ, CHIRALPAK AD and CHIRALPAK AS were evaluated under normal phase conditions, using hexane:2-propanol or hexane:ethanol as mobile phase. Diethylamine and trifluoracetic acid were also added to improve peak shape. The CHIRALCEL OJ-R, CHIRALCEL OD-R and CHIRALCEL OD-H columns were evaluated under reversed-phase conditions, using acetonitrile:H 2 O or acetonitrile:NaClO 4 solution. The protein-based stationary phases, CHIRAL AGP and ULTRON ES-OVM columns were used with mobile phases consisting of a buffer solution supplemented with an organic modifier. Among the polysaccharide-based stationary phases, CHIRALPAK AD provided better resolution for almost all drugs and metabolites studied. The ULTRON ES-OVM column was particularly suitable for the resolution of the four enantiomers of thioridazine-2-sulfoxide.

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A closer study of chiral retention mechanisms

Cited by 114 publications

References 39 publications

Enantiomeric Separation of Bicyclo[2.2.2]octane‐Based 2‐Amino‐3‐Carboxylic Acids on Macrocyclic Glycopeptide Chiral Stationary Phases

Enantiomeric Separation of Bicyclo[2.2.2]octane‐Based 2‐Amino‐3‐Carboxylic Acids on Macrocyclic Glycopeptide Chiral Stationary Phases

Predictability of Enantiomeric Chromatographic Behavior on Various Chiral Stationary Phases Using Typical Reversed Phase Modeling Software

Enantiomeric Resolution of Drugs and Metabolites in Polysaccharide- and Protein-Based Chiral Stationary Phases

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