纤维素-三(4-甲基苯甲酸酯)涂覆型手性固定相的制备研究与分离应用
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摘要
以C_8硅烷修饰的大孔硅胶作基质,涂覆制备了纤维素-三(4-甲基苯甲酸酯)手性固定相,研究了涂覆溶剂体系对固定相选择性的影响。实验选择氯仿或二氯甲烷作溶剂,分别添加N,N’-二甲基甲酰胺、苯酚、硝基苯、苯甲酸甲酯、苯乙酮涂覆制备了多个手性固定相,并以7种不同结构的手性化合物对固定相进行评价。结果表明,添加剂的种类与添加量对固定相的装柱柱效、保留以及选择性均会产生一定的影响。添加与纤维素酯等质量的苯甲酸甲酯制得的固定相性能较佳,其对于西孟坦中间体和酮咯酸消旋体具有良好的对映体拆分能力,具备工业制备分离的应用潜力。
Based on C_8 modified macroporous silica,a coated cellulose tri(4-methylbenzoate)( CTMB) chiral stationary phases( CSPs) were prepared. Influences of coating solvent and additive on the enantioselectivity of CSP were investigated. Several CSPs were prepared by coating CTMB in chloroform and dichloromethane,with N,N'-dimethylformamide( DMF),phenol,nitrobenzene,methyl benzoate and acetophenone as additives,respectively. The enantioselectivities of CSPs were evaluated by using 7 structurally different enantiomers. It was found that column efficiency,retention ability and enantioselectivity of CSPs were affected by the type and amount of additive. The addition of the same amount of methyl benzoate with CTMB would provide the CSPs with better properties,which exhibit a good enantioseparation ability for racemic simendan intermediate and ketorolac,and possess an application potential in industrial preparation and separation.
Based on C_8 modified macroporous silica,a coated cellulose tri(4-methylbenzoate)( CTMB) chiral stationary phases( CSPs) were prepared. Influences of coating solvent and additive on the enantioselectivity of CSP were investigated. Several CSPs were prepared by coating CTMB in chloroform and dichloromethane,with N,N'-dimethylformamide( DMF),phenol,nitrobenzene,methyl benzoate and acetophenone as additives,respectively. The enantioselectivities of CSPs were evaluated by using 7 structurally different enantiomers. It was found that column efficiency,retention ability and enantioselectivity of CSPs were affected by the type and amount of additive. The addition of the same amount of methyl benzoate with CTMB would provide the CSPs with better properties,which exhibit a good enantioseparation ability for racemic simendan intermediate and ketorolac,and possess an application potential in industrial preparation and separation.
引文
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[8] Murakami Y,Shibata T,Ueda K. Carbohydr. Res.,2017,439(1):35-43.
[9] Niedermeier S,Matarashvili I,Chankvetadze B,Scriba G K. J. Pharm. Biomed. Anal.,2018,158(5):294-299.
[10] Shibata T,Sei T,Nishimura H. Chromatographia,1987,24(1):552-554.
[11] Francotte E,Zhang T. J. Chromatogr. A,1995,718(2):257-266.
[12] Chen X M,Yang L,Zou H F. Chin. J. Anal. Chem.(陈小明,杨利,邹汉法.分析化学),2000,28(7):879-882.
[13] Grieb S J,Matlin S A,Belenguer A M,Ritchie H J. J. Chromatogr. A,1995,697(1/2):271-278.
[14] Zhang D D,Guo X J,Yuan B,Li F M. Chin. J. Anal. Chem.(张丹丹,郭兴杰,袁波,李发美.分析化学),2004,32(2):229-231.
[15] Meng F H,Liu X Y,Liu Y R,Feng X S,Wang L K. Chem. Bioeng.(孟繁浩,刘翔宇,刘雅茹,冯雪松,王立坤.化学与生物工程),2006,23(12):50-51.
[16] Fuelling G,Sih C J. J. Am. Chem. Soc.,1987,109(9):2845-2846.
[17] Gusman A,Yuste F,Toscano R A,Young J M,Van Horn A R. J. Med. Chem.,1986,29(4):589-591.