Tran Chieu D, Mejac Irena
Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, WI 53201-1881, USA.
J Chromatogr A. 2008 Sep 19;1204(2):204-9. doi: 10.1016/j.chroma.2008.04.013. Epub 2008 Apr 12.
A chiral ionic liquid (IL), S-[3-(chloro-2-hydroxypropyl)trimethylammonium] [bis((trifluoromethyl)sulfonyl)amide] (S-CHTATf(2)N), which can be easily and readily synthesized in a one-step process from commercially available reagents, can be successfully used both as co-electrolyte and as a chiral selector for CE. A variety of pharmaceutical products including atenolol, propranolol, warfarin, indoprofen, ketoprofen, ibuprofen and flurbiprofen, can be successfully and baseline separated with the use of this IL as electrolyte. Interestingly, while S-CHTATf(2)N can also serve as a chiral selector, enantioseparation cannot be successfully achieved with S-CHTATf(2)N as the only chiral selector. In the case of ibuprofen, a second chiral selector, namely a chiral anion (sodium cholate), is needed for the chiral separation. For furbiprofen, in addition to S-CHTATf(2)N and sodium cholate, a third and neutral chiral selector, 1-S-octyl-beta-d-thioglucopyranoside (OTG), is also needed. Due to the fact that the chirality of this chiral IL resides on the cation (i.e., -CHTA), and that needed additional chiral selector(s) are either chiral anion (i.e., cholate) or chiral neutral compound (OTG), the results obtained seem to suggest that additional chiral selector(s) are needed to provide the three-point interactions needed for chiral separations.
一种手性离子液体（IL），S-[3-(氯-2-羟丙基)三甲基铵][双((三氟甲基)磺酰基)酰胺]（S-CHTATf(2)N），它可以通过一步法由市售试剂轻松且容易地合成，既可以成功用作共电解质，也可以用作毛细管电泳的手性选择剂。使用这种离子液体作为电解质，可以成功地对包括阿替洛尔、普萘洛尔、华法林、吲哚洛芬、酮洛芬、布洛芬和氟比洛芬在内的多种药物产品进行基线分离。有趣的是，虽然S-CHTATf(2)N也可以用作手性选择剂，但仅以S-CHTATf(2)N作为唯一的手性选择剂无法成功实现对映体分离。对于布洛芬，手性分离需要第二种手性选择剂，即手性阴离子（胆酸钠）。对于氟比洛芬，除了S-CHTATf(2)N和胆酸钠外，还需要第三种中性手性选择剂，1-S-辛基-β-D-硫代葡萄糖苷（OTG）。由于这种手性离子液体的手性存在于阳离子上（即-CHTA），并且所需的额外手性选择剂要么是手性阴离子（即胆酸盐）要么是手性中性化合物（OTG），所获得的结果似乎表明需要额外的手性选择剂来提供手性分离所需的三点相互作用。
