高效液相色谱（ HPLC）被广泛认为是分离制备光学纯单一对映体的最有效方法。在高效液相色谱手性拆分中，手性固定相（ CSP）的性能直接影响到色谱柱的手性分离能力。在众多手性固定相中，键合型手性固定相具有溶剂耐受性好，分离模式灵活等优点，已经发展成为一类重要的手性固定相。本文通过两步化学反应合成了新型的光学活性丙烯酰胺衍生物———（S）-1-丙烯酰-2-（N-苯基甲酰胺基）吡咯烷（（S）-APACP），采用核磁共振氢谱表征了（ S）-APACP的化学结构；通过3步化学反应制备了键合型聚丙烯酰胺衍生物手性固定相，采用热重分析法表征了聚合物的键合量，采用 HPLC评价了键合型手性固定相的识别能力，分析了影响其手性识别能力的因素。研究结果表明，APACP聚合物成功地键合到硅胶表面制备了具有良好溶剂耐受性的键合型手性固定相，其聚合物键合量为10.2％~11.8％，该键合型手性固定相对若干种对映体显示了较好的手性识别能力。
High performance liquid chromatography( HPLC)has been widely considered as the most effective way for the separation and preparation of optically pure enantiomers. In the reso-lution by HPLC,the separation ability of a column strongly depends on the properties of a chiral stationary phase( CSP). Among many CSPs,the immobilized CSPs,which are becoming one of the most important kinds of CSPs,have the advantages of good solvent durability and enormous method flexibility. In this work,a novel optically active acrylamide derivative( S)-APACP was synthesized by two-step reactions,and its chemical structure was characterized by 1 H NMR. The polyacrylamide derivatives were immobilized on silica gel by three-step reactions to prepare immobilized CSPs,and the immobilization amount of the polymers was tested by thermogravimetric analysis. The chiral recognition ability of the immobilized CSPs was evalua-ted by HPLC,and the effects of Lewis acid and mobile phase on the chiral recognition ability were investigated. The results showed that APACP polymer was successfully immobilized on silica gel to prepare immobilized-type CSP with better solvent durability,and the amount of immobilized polymer was 10. 2% to 11. 8%. The immobilized-type CSP showed good chiral
recognition ability for several enantiomers.
参考文献
| [1] | Shen, J.;Liu, S.;Li, P.;Shen, X.;Okamoto, Y..Controlled synthesis and chiral recognition of immobilized cellulose and amylose tris(cyclohexylcarbamate)s/3-(triethoxysilyl)propylcarbamates as chiral packing materials for high-performance liquid chromatography[J].Journal of chromatography, A: Including electrophoresis and other separation methods,2012:137-144. |
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