betadex and formamide

Our aim was to establish suitable conditions for the chiral separation of 12 1,3,4-thia- and 1,3,4-selenadiazine derivatives; some of them were identified in screening tests as potential antituberculotics. To overcome possible problems with the water insolubility of most analytes, we profited by the advantages of non-aqueous capillary electrophoresis. Methanol, formamide, and a mixture of formamide with acetonitrile (1:2, v/v) were used as separation media. Hydroxyethyl-, hydroxypropyl-, and methyl-beta-cyclodextrin were applied as chiral selectors in concentrations of 200 mM. Besides the effect of these different electrophoretic media and selectors, we also investigated the consequences of using different electrolytes (25 mM ammonium acetate/1 M acetic acid and 25 mM citric acid/12.5 mM TRIS). Distinct differences of the separation factors in the different separation media were observed. Depending on structure characteristics of the analytes, we established clear classifications to these cyclodextrins (CD), which were most appropriate for the separation of the enantiomers of the particular analytes.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Acetates; Acetic Acid; Acetonitriles; beta-Cyclodextrins; Citric Acid; Cyclodextrins; Electrophoresis, Capillary; Formamides; Methanol; Organometallic Compounds; Organoselenium Compounds; Stereoisomerism; Thiadiazines; Time Factors; Tromethamine

This paper reports the application of an anionic cyclodextrin (CD), sulfated beta-cyclodextrin with a degree of substitution of four (beta-CD-(SO4-)4, in chiral separations of pharmaceutical enantiomers by non-aqueous capillary electrophoresis (NACE). Upon complexation with the anionic CD, electrophoretic mobilities of the basic enantiomers decreased, however, both separation selectivity and resolution were enhanced. The advantage of NACE chiral separations over the aqueous CE with the charged CD is that higher electric field strength and higher ionic strength could be applied due to the characteristics of the solvent formamide. The higher ionic strength leads to stacking of peaks and reduces the electrodispersion caused by the mobility mismatch between beta-CD-(SO4-)4-analyte complexes and the co-ions in the running buffer. As a result, better peak shapes and higher separation efficiency were obtained. Comparing with NACE chiral separations with neutral CDs, lower concentration of beta-CD-(SO4-)4 was needed due to the fact that the electrostatic attraction caused stronger binding between beta-CD-(SO4-)4 and the enantiomers. The effects of the experimental parameters, such as concentration of the CD, apparent pH (pH*), degree of substitutions of the CDs, percentage of water in mixed solvent systems, and type of solvents were also studied.

Topics: beta-Cyclodextrins; Cyclodextrins; Electrophoresis, Capillary; Formamides; Hydrogen-Ion Concentration; Solvents; Sulfates; Water