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Enantiomeric separation of phenylsuccinic acid by cyclodextrin-modified reversed phase high-performance liquid chromatography

  • Rui-lin Man (满瑞林)
  • Zhong-hui Wang (王钟辉)
  • Ke-wen Tang (唐课文)Email author
Article

Abstract

The chiral separation of phenylsuccinic acid (PSA) was studied by reversed phase high-performance liquid chromatography (RP-HPLC) with cyclodextrins (CDs) as chiral mobile phase additives. The effects of types of CDs, concentration of hydroxypropyl-β-cyclodextrin (HP-β-CD), percentage of organic modifier, pH value and column temperature on enantioselective separation were investigated. The quantification property of the developed RP-HPLC method was examined. The chiral recognition mechanism of PSA was also discussed. The results show that a baseline separation of PSA enantiomers is achieved on a Lichrospher C18 column (4.6 mm (inner diameter)×250 mm, 5 μm) with HP-β-CD as chiral mobile phase additive. The capacity factors of R-PSA and S-PSA are 3.94 and 4.80, respectively. The separation factor and resolution are respectively 1.22 and 8.03. The mobile phase is a mixture of acetonitrile and deionized water (20:80, volume ratio) containing 10 mmol/L HP-β-CD and 0.05% trifluoroacetic acid (pH 2.5, adjusted with triethylamine) with a flow rate of 1.0 mL/min. The ultraviolet (UV) detector is set at 254 nm. The likely roles are inclusion interaction, induction and hydrogen bonding between HP-β-CD and PSA enantiomers.

Key words

high performance liquid chromatography hydroxypropyl-β-cyclodextrin enantiomer separation phenylsuccinic acid 

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References

  1. [1]
    MIYAKO E, MARUYAMA T, KAMIYA N, GOTO M. Highly enantioselective separation using a supported liquid membrane encapsulating surfactant-enzyme complex [J]. J Am Chem Soc, 2004, 126(28): 8622–8623.CrossRefGoogle Scholar
  2. [2]
    MIRIAM L. Membranes make chiral separations simpler [J]. Manufacturing Chemist, 1995, 10(7): 25–32.Google Scholar
  3. [3]
    TANG Ke-wen, ZHANG Guo-li, HUANG Ke-long, LI Yuan-jian, YI Jian-min. Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction [J]. Science in China Series B: Chemistry, 2007, 50(6): 764–769.CrossRefGoogle Scholar
  4. [4]
    TANG Ke-wen, HUNG Ke-long. Enantioselective extraction of mandelic enantiomers based on chiral ligand exchange [J]. Journal of Central South University of Technology, 2005, 12(2): 123–128.Google Scholar
  5. [5]
    STEPHANI R, CESARE V. Determination of the enantiomers of chlorpheniramine and its main monodesmethyl metabolite in urine using achiral-chiral liquid chromatography [J]. Journal of Chromatography B, 1998, 707(2): 235–240.Google Scholar
  6. [6]
    JANDERA P, BUNCĚKOVÁ S, PLANETA J. Separation of isomeric naphthalenesulphonic acids by micro high-performance liquid chromatography with mobile phases containing cyclodextrin [J]. Journal of Chromatography A, 2000, 871(2): 139–152.CrossRefGoogle Scholar
  7. [7]
    AMEYIBOR E, STEWART J T. Resolution and quantitation of pentazocine enantiomers in human serum by reversed-phase high-performance liquid chromatography using sulfated β-cyclodextrin as chiral mobile phase additive and solid-phase extraction [J]. Journal of Chromatography B, 1997, 703(2): 273–278.CrossRefGoogle Scholar
  8. [8]
    AMEYIBOR E, STEWART J T. HPLC determination of ketoprofen enantiomers in human serum using a nonporous octadecylsilane 1.5 mm column with hydroxypropyl β-cyclodextrin as mobile phase additive [J]. Journal of Pharmaceutical and Biomedical Analysis, 1998, 17(1): 83–88.CrossRefGoogle Scholar
  9. [9]
    ZHONG Q Q, HE L F, BEESLEY T E, TRAHANOVSKY W S, SUN P, WANG C L, ARMSTRONG D W. Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography [J]. Journal of Chromatography A, 2006, 1115(1): 19–45.CrossRefGoogle Scholar
  10. [10]
    HEALY L O, MURRIHY J P, TAN A M, COCKER D, MCENERY M, GLENNON J D. Enantiomeric separation of R, S-naproxen by conventional and nano-liquid chromatography with methyl-b-cyclodextrin as a mobile phase additive [J]. Journal of Chromatography A, 2001, 924(2): 459–464.CrossRefGoogle Scholar
  11. [11]
    CHEN De-ying, JIANG Shu-min, CHEN Yu-ying, HU Yu-zhu. HPLC determination of sertraline in bulk drug, tablets and capsules using hydroxypropyl-β-cyclodextrin as mobile phase additive [J]. Journal of Pharmaceutical and Biomedical Analysis, 2004, 34(1): 239–245.CrossRefGoogle Scholar
  12. [12]
    YE Jin-cui, CHEN Guo-sheng, ZENG Su. Enantiomeric separation of norgestrel by reversed phase high-performance liquid chromatography using eluents containing hydroxypropyl-beta-cyclodextrin in stereoselective skin permeation study [J]. Journal of Chromatography B, 2006, 843(2): 289–294.CrossRefGoogle Scholar
  13. [13]
    SPENCER B J, PURDY W C. Effect of the degree of substitution of cyclodextrin derivatives on chiral separations by high-performance liquid chromatography [J]. Liq Chromatogr, 1995, 18(16): 4063–4080.CrossRefGoogle Scholar
  14. [14]
    RUAN Yuan-ping, AO Xiao-ping, ZHANG Xue-man, ZHANG Pei-qiang. Liquid chromatographic resolution of enantiomeric 1, 1′-bi-2-naphthol and phenylsuccinic acid on a coated reversed-phase column with 2, 6-O-butyled-β-cyclodextrins [J]. Chinese Journal of Analytical Chemistry, 2004, 32(7): 949–952. (in Chinese)Google Scholar
  15. [15]
    BIELEJEWSKA A, NOWAKOWSKI R, DUSZCZYK K, SYBILSKA D. Joint use of cyclodextrin additives in chiral discrimination by reversed-phase high-performance liquid chromatography: Temperature effects [J]. Journal of Chromatography A, 1999, 840(2): 159–170.CrossRefGoogle Scholar
  16. [16]
    CHEN J Z, OHNMACHT C M, HAGE D S. Characterization of drug interactions with soluble β-cyclodextrin by high-performance affinity chromatography [J]. Journal of Chromatography A, 2004, 1033(1): 115–126.CrossRefGoogle Scholar

Copyright information

© Central South University Press and Springer-Verlag GmbH 2009

Authors and Affiliations

  • Rui-lin Man (满瑞林)
    • 1
  • Zhong-hui Wang (王钟辉)
    • 1
  • Ke-wen Tang (唐课文)
    • 1
    • 2
    Email author
  1. 1.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina
  2. 2.Department of Chemistry and Chemical EngineeringHunan Institute of Science and TechnologyYueyangChina

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