淀粉及纤维素三(3-三氟甲基苯基氨基甲酸酯)手性固定相的制备及其性能评价

Preparation and evaluation of amylose and cellulose tris(3-trifluoromethylphenylcarbamates)-based chiral stationary phases

为了扩展多糖类手性固定相的种类,制备了基于淀粉及纤维素三(3-三氟甲基苯基氨基甲酸酯)的涂敷型手性固定相,以正己烷-异丙醇混合液为流动相,对8种手性化合物进行了高效液相色谱拆分。研究表明:虽然与应用最广泛的分别以淀粉及纤维素三(3,5-二甲基苯基氨基甲酸酯)为手性选择因子的商品化手性柱Chiralpak AD和Chiralcel OD相比,所制备的手性固定相的手性分离能力较低,但纤维素三(3-三氟甲基苯基氨基甲酸酯)手性固定相显示出特异的手性识别能力,一些手性化合物在此固定相上得到了比在Chiracel OD上更好的分离;所制备的手性固定相的手性识别能力随流动相中异丙醇含量的降低而变好,当流动相中正己烷与异丙醇的体积比为95∶5时所制备的手性固定相显示出相对较高的手性识别能力;总体来说,淀粉三(3-三氟甲基苯基氨基甲酸酯)手性固定相的手性识别能力稍强于纤维素三(3-三氟甲基苯基氨基甲酸酯)手性固定相,同时两种手性固定相的手性识别能力具有一定的互补性。

To broaden the category of polysaccharide-based chiral stationary phases（CSPs）,coated CSPs based on tris（3-trifluoromethylphenylcarbamates） of amylose and cellulose were prepared for enantioseparation in high performance liquid chromatography.Their performances were evaluated by eight racemates using hexane-isopropanol as mobile phase.Compared with the most widely used,commercially available polysaccharide-based CSPs,Chiralpak AD and Chiralcel OD,utilizing tris（3,5-dimethylphenylcarbamates） of amylose and cellulose as the chiral selector,respectively,the obtained CSPs exhibited lower enantioseparation abilities.However,cellulose tris（3-trifluoromethylphenylcarbamate）-based CSP exhibited characteristic enantioseparation and some chiral compounds were better resolved on this CSP than on Chiralcel OD.The chiral recognition abilities of the obtained CSPs were increased with the decrease of the portion of isopropanol in the mobile phase and relatively high enantioseparation was obtained with the mobile phase of hexane-isopropanol（95∶5,v/v）.The obtained amylosic phase demonstrated slightly higher chiral resolving ability than the cellulosic one for the test racemates.In addition,it was revealed that the enantioseparations of the cellulosic and amylosic CSPs were complementary.