Enantioseparation of phenylsuccinic acid by high speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector
Enantioseparation of phenylsuccinic acid by high speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector
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DOI：
10.1016/j.chroma.2011.06.023
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发表时间：
2011-08-19
影响因子：
4.1
通讯作者：
Lu, Youming
中科院分区：
文献类型：
--
作者：
Tong, Shengqiang;Yan, Jizhong;Lu, Youming
以羟丙基-β-环糊精（HP-β-CD）为手性选择剂，采用高速逆流色谱法（HSCCC）成功拆分了苯丁二酸（PSA）。选择了正己烷-甲基叔丁基醚-0.1 mol L（-1）磷酸盐缓冲液（pH = 2.51）（0.5：1.5：2，v/v/v）组成的两相溶剂体系。考察了手性选择剂浓度、水相pH值、分离温度等因素对手性拆分的影响，并计算了包合物的热力学参数。用分析仪器测定了配合物的形成常数。研究了两种HSCCC洗脱模式，并对峰分离方程进行了讨论。在最佳分离条件下，用制备装置分离出712 mg PSA外消旋体。经HPLC测定，（+）-PSA和（-）-PSA的纯度均大于98.5%，对映体过量分别达到97.6%和98.6%。从CCC级分中回收目标化合物达到80-82%，得到285 mg（+）-PSA和292 mg（+）-PSA。(C)2011 Elsevier B. V.保留所有权利。
High speed counter-current chromatography (HSCCC) was successfully applied to resolution of phenylsuccinic acid (PSA) with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) as chiral selector (CS). The two-phase solvent system composed of n-hexane-methyl tert-butyl ether-0.1 mol L(-1) phosphate buffer solution with pH = 2.51 (0.5:1.5:2, v/v/v) was selected. Influence factors involved in the chiral separation were investigated, including the concentration of chiral selector, pH value of the aqueous phase, the separation temperature, and the thermodynamic parameters of inclusion complex were calculated. The complex formation constants were determined using analytical instrument. Two HSCCC elution modes were studied and peak resolution equation was discussed. Under optimum separation conditions, 712 mg of PSA racemate was separated using preparative apparatus. The purities of both of the fractions including (+)-PSA and (-)-PSA from the preparative CCC separation were over 98.5% determined by HPLC and enantiomeric excess of (+)-PSA and (-)-PSA reached 97.6% and 98.6%, respectively. Recovery for the target compounds from the CCC fractions reached 80-82% yielding 285 mg of (+)-PSA and 292 mg of ()-PSA. (C) 2011 Elsevier B.V. All rights reserved.