手性流动相添加剂高效液相色谱法分离苯基琥珀酸对映体

High Performance Liquid Chromatographic Separation of Racemic Phenylsuccinic Acid Using Chiral Mobile Phase Additives

以七 (2,3,6_三_O_甲基 )_β_环糊精 (TM_β_CD)作为手性流动相添加剂 ,反相高效液相色谱研究苯基琥珀酸 (PSA)对映体拆分 ;在Nova-pakC18 色谱柱上 ,采用0.30mmol/LTM_β_CD、含0.05 %三氟乙酸的乙腈 -水(体积比16∶84)为流动相 ,(R)_( -)_PSA和(S)_( +)_PSA的容量因子分别为5.43和6.42 ,对映体分离因子为1.18 ,分离度为2.50 ;对比PSA在 β_CD手性流动相法和2,6_丁基化_β_CD涂渍C18柱的色谱行为 ,探讨环糊精分子对PSA的手性拆分机理 ;本法已用于测定L_脯氨酸化学拆分苯基琥珀酸对映体产品的光学纯度。

The enantiomeric separation of phenylsuccinic acid(PSA)was studied byRP-HPLC usinghepˉtakis-(2,3,6-tri-O-methyl)-β-cyclodextrin(TM-β-CD)as a chiral mobile phase additive.The operating conditions were Nova-pak C 18 column(3.9mm i.d.×150mm,4μm)at room temperature(ca.25℃),0.30mmol/LTM-β-CD+0.05%TFA+16%CH 3 CNas a mobile phase with a flowrate of1.0mL/min and UVdetection at254nm.The capacity factors of(R)-(-)-PSA and(S)-(+)-PSA were5.43and6.42,respectively.The separation factor and resolution were respectively1.18and2.50.Comparingβ- CD as a chiral mobile phase additive and2,6-butylatedβ-CD coated ODS column,the chiral recognition mechanism of PSA was investigated.The likely roles were inclusion interaction and hydrogen bonding be- tweenβ-CD and PSA.This method has been applied to determine the enantiomeric purity of PSA obtained from a resolution process.