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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.
J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 01; 962:44-51.JC

Abstract

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 (150×4.6mm i.d., 5μm). The mobile phase was a mixture of acetonitrile and 0.10molL(-1) of phosphate buffer at pH 2.68 containing 20mmolL(-1) of HP-β-CD or SBE-β-CD. Semi-preparative enantioseparation of about 10mg 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 stoichiometries for all the inclusion complex of cyclodextrin-enantiomers were 1:1.

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Authors+Show Affiliations

Tong S
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, China; Laboratory of Bioseparation Technologies, Biochemistry and Biophysics Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD 20892, USA.
Zhang H
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, China.
Shen M
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, China.
Ito Y
Laboratory of Bioseparation Technologies, Biochemistry and Biophysics Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD 20892, USA.
Yan J
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, China. Electronic address: zyx@zjut.edu.cn.

MeSH

2-Hydroxypropyl-beta-cyclodextrinChromatography, High Pressure LiquidChromatography, Reverse-PhaseMandelic AcidsStereoisomerismbeta-Cyclodextrins

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24893270

Citation

Tong, Shengqiang, et al. "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." Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, vol. 962, 2014, pp. 44-51.
Tong S, Zhang H, Shen M, et al. 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. J Chromatogr B Analyt Technol Biomed Life Sci. 2014;962:44-51.
Tong, S., Zhang, H., Shen, M., Ito, Y., & Yan, J. (2014). 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. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 962, 44-51. https://doi.org/10.1016/j.jchromb.2014.05.026
Tong S, et al. 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. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 1;962:44-51. PubMed PMID: 24893270.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Tong,Shengqiang, AU - Zhang,Hu, AU - Shen,Mangmang, AU - Ito,Yoichiro, AU - Yan,Jizhong, Y1 - 2014/05/22/ PY - 2014/02/08/received PY - 2014/04/11/revised PY - 2014/05/07/accepted PY - 2014/6/4/entrez PY - 2014/6/4/pubmed PY - 2015/1/27/medline KW - Chiral separation KW - High performance liquid chromatography KW - Hydroxypropyl-β-cyclodextrin KW - Mandelic acid derivatives KW - Sulfobutyl ether-β-cyclodextrin SP - 44 EP - 51 JF - Journal of chromatography. B, Analytical technologies in the biomedical and life sciences JO - J Chromatogr B Analyt Technol Biomed Life Sci VL - 962 N2 - 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 (150×4.6mm i.d., 5μm). The mobile phase was a mixture of acetonitrile and 0.10molL(-1) of phosphate buffer at pH 2.68 containing 20mmolL(-1) of HP-β-CD or SBE-β-CD. Semi-preparative enantioseparation of about 10mg 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 stoichiometries for all the inclusion complex of cyclodextrin-enantiomers were 1:1. SN - 1873-376X UR - https://www.unboundmedicine.com/medline/citation/24893270/Enantioseparation_of_mandelic_acid_derivatives_by_high_performance_liquid_chromatography_with_substituted_��_cyclodextrin_as_chiral_mobile_phase_additive_and_evaluation_of_inclusion_complex_formation_ DB - PRIME DP - Unbound Medicine ER -
Grapherence [↓3 ↑11]

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