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

胶束电动色谱手性分离新型手性表面活性剂的开发

• 批准号: 10554047
• 负责人: TERABE Shigeru
• 金额: $ 8.83万
• 依托单位: HIMEJI INSTITUTE OF TECHNOLOGY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B).
• 财政年份: 1998
• 资助国家: 日本
• 起止时间: 1998 至 2000
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-10554047/
• 关键词: CAPILLARY ELECTROPHORESIS; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; ENANTIOMER SEPARATION; CHIRAL SURFACTANT; CAPILLARY ELECTROCHROMATOGRAPHY; 硫酸N-デカノイル-N-メチルグルカミドナトリウム

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.

三种新型的手性表面活性剂，酒石酸衍生物，烷基葡糖苷，烷酰基葡糖酰胺被用作胶束电动色谱分离对映体的伪固定相。在酒石酸衍生物中，双（三乙基铵）2，3-双十二烷氧基-1，4-丁烯二硫酸酯解析了几种PTH-氨基酸、抗疟伯氨喹、支气管扩张剂丙卡特罗和利尿剂吲达帕胺的对映体。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-氨基酸的对映选择性几乎相等。除了肌肉松弛剂托哌酮之外，N-十二烷酰基-N-葡糖酰胺钠还能够拆分PTH-氨基酸和丹磺酰氨基酸的对映体。该表面活性剂可在酸性或碱性条件下使用。采用两种不同类型的毛细管电色谱柱对映体进行了分离。100 μm i.d.填充Daicel OD型手性固定相的毛细管和内径为20 μm的开放管状毛细管。采用通过吸附用抗生物素蛋白包被的材料。两种柱均显示出比相应的HPLC柱高得多的效率。

项目成果

Koji Otsuka: "Effects of Compositions of Dimethyl-β-cyclodextrins on Enantiomer Separations by Cyclodextrin Modified capillary Electrophoresis"Journal of Pharmaceutical and Biomedical Analysis. 17. 1177-1190 (1998)

Koji Otsuka：“二甲基-β-环糊精组合物对环糊精修饰毛细管电泳对映异构体分离的影响”《药物与生物医学分析杂志》17. 1177-1190 (1998)。

Takuya Yamaguchi: "Simultaneous Separation of Seven Pairs of D,L-Dansylamino Acids by Capillary Electrophoresis with 2,3,6-Tri-O-methyl-β-cyclodextrin in Acidic Media in the Presence or Absence of Surfactants."Chromatography. 19. 15-18 (1998)

Takuy​​a Yamaguchi：“在存在或不存在表面活性剂的酸性介质中，通过毛细管电泳同时分离七对 D,L-丹酰氨基酸。”色谱法。 .15-18 (1998)

Yoshihide Tanaka: "Separation of Acidic Enantiomers by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique"Journal of Chromatography A. 802. 83-88 (1998)

Yoshihide Tanaka：“采用部分填充技术通过毛细管电泳-质谱法分离酸性对映体”色谱杂志 A. 802. 83-88 (1998)

Liu Zhen: "Chiral Separation by Open Tubular Capillary Electrochromatography with Adsorbed Avidin as a Stationary Phase"Journal of Separation Science. 24. 17-26 (2001)

刘震：“以吸附抗生物素蛋白为固定相的开管毛细管电色谱法进行手性分离”《分离科学》杂志。

Zhen Liu: "Chiral Separation by Open Tubular Capillary Electrochromatography with Adsorbed Avidin as a Stationary Phase."Journal of Separation Science. 24. 17-26 (2001)

刘震：“以吸附的抗生物素蛋白作为固定相，通过开管毛细管电色谱进行手性分离。”分离科学杂志。