DEVELOPMENT OF NEW CHIRAL SURFACTANTS FOR CHIRAL SEPARATION BY MICELLAR ELECTROKINETIC CHROMATOGRAPHY

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Three new types of chiral surfactants, tartaric acid derivatives, alkyl glucosides, and alkanoyl glucamides were employed as pseudostationary phases in micellar electrokinetic chromatography for the separation of enantiomers. Among the tartaric acid derivatives, bis (triethylammonium) 2,3-didodecyloxy-1,4-butylene disulfate resolved enantiomers of several PTH-amino acids, antimalarial primaquine, a bronchodilator, procaterol, and a diuretic, indapamide. Sodium dodecyl D-glucopyranoside 6-sulfate and sodium hexadecyl D-glucopyranoside 6-sulfate showed almost equal enantioselectivities resolving several PTH-amino acids. Sodium N-dodecanoyl-N-glucamide was able to resolve enantiomers of both PTH-amino acids and dansyl amino acids, in addition to a muscle relaxant, tolperisone. The surfactant was usable either in acidic or in alkaline conditions. Capillary electrochromatography was applied to enantiomer separation using two different types of columns. A 100 μm i.d. capillary packed with a Daicel OD-type chiral stationary phase and an open tubular capillary of 20 μm i.d. coated with avidin by adsorption were employed. Both columns showed much higher efficiency than the corresponding HPLC columns.