Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation.
Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation.
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DOI：
10.1016/j.jchromb.2014.05.026
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发表时间：
2014-07-01
影响因子：
3
通讯作者：
Yan, Jizhong
中科院分区：
文献类型：
--
作者：
Tong, Shengqiang;Zhang, Hu;Shen, Mangmang;Ito, Yoichiro;Yan, Jizhong
关键词：
采用反相高效液相色谱法，以羟丙基-β-环糊精（HP-β-CD）或磺基丁基醚-β-环糊精（SBE-β-CD）为手性流动相添加剂，对十种杏仁酸衍生物的对映体进行分离，考察环糊精与对映体之间的包合物形成。考察了流动相组成、环糊精浓度、柱温等因素对环糊精保留率和对映体选择性的影响。对映体的峰分辨率和保留时间受流动相中pH、有机改性剂和β-环糊精类型的影响较大，而缓冲液的浓度和温度对峰分辨率的影响较小。在Shimpack lc - ods色谱柱（150×4.6 mm id, 5 μm）上成功分离了对映体。流动相为乙腈与0.10 mol L-1磷酸缓冲液的混合物，pH为2.68，其中含有20 mmol L-1 HP-β-CD或SBE-β-CD。分别建立了α-环己基扁桃酸和α-环戊基扁桃酸约10 mg的半制备对映体分离。研究了环糊精-对映体配合物的化学计量学和结合常数。结果表明，环糊精-对映体包合物的化学计量比均为1:1。
The enantioseparation of ten mandelic acid derivatives was performed by reverse phase high performance liquid chromatography with hydroxypropyl-β-cyclodextrin (HP-β-CD) or sulfobutyl ether-β-cyclodextrin (SBE-β-CD) as chiral mobile phase additives, in which inclusion complex formations between cyclodextrins and enantiomers were evaluated. The effects of various factors such as the composition of mobile phase, concentration of cyclodextrins and column temperature on retention and enantioselectivity were studied. The peak resolutions and retention time of the enantiomers were strongly affected by the pH, the organic modifier and the type of β-cyclodextrin in the mobile phase, while the concentration of buffer solution and temperature had a relatively low effect on resolutions. Enantioseparations were successfully achieved on a Shimpack CLC-ODS column (150×4.6 mm i.d., 5 μm). The mobile phase was a mixture of acetonitrile and 0.10 mol L-1 of phosphate buffer at pH 2.68 containing 20 mmol L-1 of HP-β-CD or SBE-β-CD. Semi-preparative enantioseparation of about 10 mg of α-cyclohexylmandelic acid and α-cyclopentylmandelic acid were established individually. Cyclodextrin-enantiomer complex stoichiometries as well as binding constants were investigated. Results showed that stoichiomertries for all the inclusion complex of cyclodextrin-enantiomers were 1:1.
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影响因子：
4.1
作者：
Tong, Shengqiang;Yan, Jizhong;Lu, Youming
通讯作者：
Lu, Youming
影响因子：
4.1
作者：
Tong, Shengqiang;Guan, Yi-Xin;Zhao, Liying
通讯作者：
Zhao, Liying
DOI：
10.1016/j.chroma.2010.02.077
发表时间：
2010-04-30
期刊：
Journal of chromatography. A
影响因子：
--
作者：
Tong S;Yan J;Guan YX;Fu Y;Ito Y
通讯作者：
Ito Y
DOI：
10.1016/s0378-4347(00)00103-1
发表时间：
2000-04-14
期刊：
JOURNAL OF CHROMATOGRAPHY B
影响因子：
--
作者：
Herráez-Hernández, R;Campíns-Falcó, P
通讯作者：
Campíns-Falcó, P
影响因子：
2.8
作者：
Jiao, FP;Huang, KL;Yu, JG
通讯作者：
Yu, JG