2,6-O-丁基-β-环糊精涂渍反相柱高效液相色谱拆分联萘二酚和苯基琥珀酸对映体

Liquid Chromatographic Resolution of Enantiomeric 1,1'-Bi-2-naphthol and Phenylsuccinic Acid on a Coated Reversed-phase Column with 2,6-O-Butyled β-Cyclodextrins

利用合成的 2 ,6 O 丁基 β 环糊精动态涂渍反相色谱柱 ,β CD在C18和C8填料表面“永久”吸附形成一手性固定相 ,以联萘二酚和苯基琥珀酸为对象进行高效液相色谱拆分研究。当采用乙腈 水 (体积 33∶6 7)流动相时 ,联萘酚对映体在 2 ,6 O 丁基 β 环糊精涂渍ExsilODS柱上分离的容量因子分别为 14 .2 35和 15 6 2 9,分离选择性为 1.0 98;而采用乙腈 0 .1%三氟乙酸水溶液 (体积比 15∶85 )流动相时 ,苯基琥珀对映体的容量因子分别为 7.0 2 3和 8.14 9,分离选择性为 1.16 0。文中优化了色谱条件 ,探讨了有关的手性色谱拆分机理。该法可用于实际样品的对映体纯度测定。

2,6-O-butyled β-cyclodextrin,which was synthesized in dimethyl sulfoxide (DMSO),was dynamically coated on the octadecylsilanized and octadsilanized silica columns through hydrophobic interaction. These coated columns can be used to enantiomeric resolution of 1,1′-bi-2-naphthol and phenylsuccinic acid by reversed -phase high performance liquid chromatography. On the Exsil ODS coated with the 2,6-O- butyled β-cyclodextrin,the capacity factors of 1,1′-bi-2-naphthols are 14.235 and 15.629,respectively,and enantioselectivity is 1.098 with acetonitrile-water (33∶67,V/V ) as mobile phase; the capacity factors of phenylsuccinic acids are 7.023 and 8.149,respectively,and enantioselectivity is 1.160 with acetonitrle-0.1% trifluoroacetic acid solution (15∶85,V/V ) as mobile phase. The chromatographic property of the coated chiral stationary phase and the mechanisms of enantiomeric separation was discussed. The coated 2,6-O-butyled β- cyclodextrin can be removed by methanol flowing through the column,the original column can be regenerated and used repeatedly . This method is applied to determine the enantiomeric purity of the products from the resolution of racemic 1,1′-bi-2-naphthol and phenylsuccinic acid.