Evaluation of the liquid-chromatographic resolution of indenoindolic racemic compounds on three protein-based chiral stationary phases

Bioanalytical Chemistry, Astra Hässle AB, Mölndal, Sweden.
Journal of Pharmaceutical and Biomedical Analysis (Impact Factor: 2.98). 05/1995; 13(4-5):551-61. DOI: 10.1016/0731-7085(95)01259-N
Source: PubMed


Three liquid-chromatography columns, containing immobilized proteins as chiral stationary phases (CSPs) were investigated for the direct separation of enantiomers of racemic indenoindolic compounds. By using an experimental design the effects of column temperature, pH, ionic strength, and type and concentration of organic solvent in the mobile phase on retention and resolution of racemic substances were systematically studied. The three CSPs investigated consisted of alpha(1)-acid glycoprotein (Chiral-AGP), bovine serum albumin (BSA-DSC) and ovomucoid (Ultron ES-OVM). The two enantiomers of all studied compounds could be separated on at least one of the three CSPs, which have different enantioselective properties.

3 Reads
  • [Show abstract] [Hide abstract]
    ABSTRACT: The effect of perchlorate anion as a mobile phase modifier on the retention of dansyl norvaline and dansyl tryptophan enantiomers on a human serum albumin (HSA) column was studied by varying the chaotropic agent concentrations. The thermodynamic parameters for the transfer of a solute from the mobile to the HSA stationary phases were determined from linear van't Hoff plots. An enthalpy-entropy compensation study revealed that the type of interaction between the solute and HSA was independent of the molecular structure. The parabolic variations observed with the enthalpic and entropic terms of dansyl amino acid transfer in relation to the concentration of perchlorate anion were considered to be the result of the change from reversed to normal-phase conditions for this chromatographic system.
    Journal of Chromatography A 06/1998; 808(1-2):113-20. DOI:10.1016/S0021-9673(98)00117-4 · 4.17 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: The enantioseparation of pirlindole by liquid chromatography (LC) was investigated using three different chiral stationary phases (CSPs) containing either cellulose tris-(3,5-dimethylphenylcarbamate) (Chiralcel OD-R), ovomucoid (OVM) or beta-cyclodextrin (beta-CD). The effects of the mobile phase pH on retention, enantioselectivity and resolution were studied. Methanol and acetonitrile were tested as organic modifiers while the influence of the addition to the mobile phase of sodium alkanesulfonates or sodium perchlorate was also investigated. Sodium perchlorate was only used on the Chiralcel OD-R column while sodium alkanesulfonates were tested as mobile phase additives on the three kinds of CSPs. The enantioseparation of pirlindole could be obtained on all CSPs tested, the best results with respect to chiral resolution being achieved on the Chiralcel OD-R and the OVM columns. The use of sodium octanesulfonate (NaOS) was found to improve the enantioseparation of pirlindole on the OVM column while enantioselectivity was considerably enhanced by addition of sodium perchlorate on the Chiralcel OD-R column.
    Journal of Pharmaceutical and Biomedical Analysis 01/1999; 18(4-5):605-14. DOI:10.1016/S0731-7085(98)00213-1 · 2.98 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Proteins display interesting chiral discrimination properties owing to multiple possibilities of intermolecular interactions with chiral compounds. This review deals with proteins which have been used as immobilized chiral selectors for the enantioseparation of drugs in liquid chromatography and capillary electrophoresis. The main procedures allowing the immobilization of proteins onto matrices, such as silica and zirconia particles, membranes and capillaries are first presented. Then the factors affecting the enantioseparation of drugs in liquid chromatography, using various protein-based chiral stationary phases (CSPs), are reviewed and discussed. Last, chiral separations already achieved using immobilized protein selectors in affinity capillary electrochromatography (ACEC) are presented and compared in terms of efficiency, stability and reproducibility.
    Journal of Chromatography B 12/2003; 797(1-2):131-59. DOI:10.1016/j.jchromb.2003.08.035 · 2.73 Impact Factor
Show more