Enantiomeric separation of phenylsuccinic acid by cyclodextrin-modified reversed phase high-performance liquid chromatography |
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Authors: | Rui-lin Man Zhong-hui Wang and Ke-wen Tang |
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Affiliation: | (1) School of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China;(2) Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414000, China |
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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.
Foundation item: Project(20776038) supported by the National Natural Science Foundation of China |
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Keywords: | high performance liquid chromatography hydroxypropyl-β -cyclodextrin enantiomer separation phenylsuccinic acid |
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