Clothier J G, Daley L M, Tomellini S A
Department of Chemistry, University of New Hampshire, Durham 03824, USA.
J Chromatogr B Biomed Appl. 1996 Aug 9;683(1):37-45. doi: 10.1016/0378-4347(96)00174-0.
The chiral resolving abilities of micellar solutions of four different bile salts alone and in mixtures with polyoxyethylene-4-dodecyl ether (C12E4) and methanol were investigated using MECC. The four bile salts investigated were the unconjugated sodium salts of cholic, deoxycholic, chenodeoxycholic and ursodeoxycholic acids. The test solutes included verapamil, norverapamil, gallopamil, bi-2-naphthol, atenolol and BAYK8644. The relative hydrophobicities of the micellar aggregates formed in solutions of binary mixtures of each bile salt with C12E4 were investigated by fluorescence spectroscopy using pyrene as a probe molecule. The observed enantiomeric resolution for the test compounds using these binary mixtures as MECC pseudo-stationary phases was determined. Correlations between micellar hydrophobicity for these solutions and chiral resolution of these test solutes are presented. The addition of C12E4 with or without methanol to solutions of sodium cholate and sodium deoxycholate enhanced the chiral resolution observed for compounds containing a longer hydrocarbon chain separating some of the major functional groups from the chiral center. The pure bile salt solutions generally provided better chiral resolution for the compounds where the major functional groups, such as aromatic rings, were closer to the chiral center.
使用胶束电动毛细管色谱法（MECC）研究了四种不同胆盐单独以及与聚氧乙烯-4-十二烷基醚（C12E4）和甲醇混合后的胶束溶液的手性拆分能力。所研究的四种胆盐是胆酸、脱氧胆酸、鹅去氧胆酸和熊去氧胆酸的未结合钠盐。测试溶质包括维拉帕米、去甲维拉帕米、加洛帕米、联二萘酚、阿替洛尔和BAYK8644。以芘作为探针分子，通过荧光光谱法研究了每种胆盐与C12E4二元混合物溶液中形成的胶束聚集体的相对疏水性。测定了使用这些二元混合物作为MECC假固定相时测试化合物的对映体拆分情况。给出了这些溶液的胶束疏水性与这些测试溶质的手性拆分之间的相关性。向胆酸钠和脱氧胆酸钠溶液中添加有或没有甲醇的C12E4，增强了对含有较长烃链的化合物的手性拆分能力，该烃链将一些主要官能团与手性中心隔开。纯胆盐溶液通常为主要官能团（如芳香环）更靠近手性中心的化合物提供更好的手性拆分效果。
