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

采用三种新型手性表面活性剂酒石酸衍生物、烷基糖苷和烷醇基葡萄糖酰胺作为假固定相，应用胶束电动色谱法分离对映体。在酒石酸衍生物中，二（三乙基铵）2,3-二十二烷基氧基-1,4-二磺酸丁二烯分解了几种pth氨基酸的对映体，抗疟药伯氨喹，支气管扩张剂procaterol和利尿剂吲达帕胺。十二烷基d -吡喃葡萄糖苷6-硫酸钠和十六烷基d -吡喃葡萄糖苷6-硫酸钠对几种pth氨基酸具有几乎相同的对映选择性。n -十二烷基- n -氨基葡萄糖酰胺钠能够分解甲状旁腺素氨基酸和丹酰氨基酸的对映体，以及肌肉松弛剂托培里森酮。该表面活性剂在酸性和碱性条件下均可使用。采用两种不同类型的毛细管电色谱柱对映体进行分离。采用Daicel od型手性固定相填充的100 μm毛细管和吸附涂覆亲和素的20 μm开管毛细管。两种色谱柱的效率均高于相应的高效液相色谱柱。

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.