聚甲基丙烯酸葡萄糖酯及聚甲基丙烯酸纤维二糖酯高效液相色谱手性固定相的性能测评

Evaluations of poly(methyl methacrylate) bearing glucose pendant or cellobiose pendant in high performance liquid chromatography as polymeric chiral stationary phases

首先合成了甲基丙烯酸葡萄糖酯和甲基丙烯酸纤维二糖酯,然后通过甲基丙烯酸-3-(三甲氧基硅基)丙酯分别聚合在硅胶上,并将其作为高效液相色谱手性固定相。分别以正己烷-异丙醇(体积比为90∶10)、正己烷-异丙醇-三乙胺(体积比为90∶10∶0.2)和正己烷-异丙醇-三氟乙酸(体积比为90∶10∶0.2)溶液作为流动相,对15种包含醇类、胺类、酰胺类和酮类的外消旋体化合物进行手性拆分。拆分结果表明,葡萄糖和纤维二糖聚合物固定相对大多数醇类和胺类以及部分酰胺类和酮类外消旋体化合物有较好的手性识别能力,并且二者的手性识别能力还具有一定的互补性。该研究表明,单糖和二糖聚合物固定相可成为一类新型的高效液相色谱手性固定相。

The glucopyranos units consisting of cyclodextrin and polysaccharide derivatives have been extensively used as chromatographic chiral stationary phases. The synthetic polymeric chiral stationary phases based on methyl methacrylate bearing glucose or cellobiose pendants for high performance liquid chromatography （HPLC） were prepared by radical polymerization. Fifteen racemic chiral compounds including alcohols, amines, amides and ketones, were resolved on the two chiral stationary phases using hexane-isopropanol （90/10, v/v） , hexane- isopropanol-triethylamine （90/10/0.2, v/v/v） or hexane-isopropanol-trifluoroacetic acid （ 90/ 10/0.2, v/v/v） as mobile phase, separately. The results showed that both chiral stationary phases possessed good enantioselectivity for most of the racemic alcohols and amines. A few amides and ketones could also be separated. There was some compensation of the chiral discriminating abilities between the two chiral stationary phases. This work indicates that polymers of mono- and disaccharide derivatives can soon become a very attractive new chiral stationary phase for HPLC.