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J Chromatogr A. 2014 Sep 19;1360:110-8. doi: 10.1016/j.chroma.2014.07.057. Epub 2014 Jul 24.

Chiral ligand exchange high-speed countercurrent chromatography: mechanism and application in enantioseparation of aromatic α-hydroxyl acids.

Author information

  • 1College 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.
  • 2College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China.
  • 3Laboratory of Bioseparation Technologies, Biochemistry and Biophysics Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD 20892, USA. Electronic address: itoy@nhlbi.nih.gov.
  • 4College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China. Electronic address: zyx@zjut.edu.cn.

Abstract

This work concentrates on the separation mechanism and application of chiral ligand exchange high-speed countercurrent chromatography in enantioseparation of ten racemic aromatic α-hydroxyl acids, including mandelic acid, 2-chloromandelic acid, 4-methoxymandelic acid, 4-hydroxymandelic acid, α-methylmandelic acid, 4-hydroxy-3-methoxy-mandelic acid, 3-chloromandelic acid, 4-bromomandelic acid, α-cyclopentylmandelic acid and α-cyclohexylmandelic acid, in which five of the racemates were successfully enantioseparated by analytical apparatus with an optimized solvent system. The two-phase solvent system was composed of butanol-water (1:1, v/v) or hexane-n-butanol-water (0.5:0.5:1, v/v), to which N-n-dodecyl-l-proline was added in the organic phase as chiral ligand and cupric acetate was added in the aqueous phase as a transition metal ion. Various influence factors in high-speed countercurrent chromatography were optimized by enantioselective liquid-liquid extraction. The separation mechanism for chiral ligand exchange high-speed countercurrent chromatography was proposed based on the results of present studies. Successful enantioseparations of 72mg of mandelic acid, 76mg of 2-chloromandelic acid and 74mg of 4-methoxymandelic acid were achieved individually with high resolution by preparative high-speed countercurrent chromatography. The HPLC purity of all enantiomers was over 96% with the recovery in the range of 82-90% from the collected fractions.

Copyright © 2014 Elsevier B.V. All rights reserved.

KEYWORDS:

Aromatic α-hydroxyl acids; Chiral ligand exchange; Enantioseparation; High-speed countercurrent chromatography; Separation mechanism

PMID:
25087742
[PubMed - indexed for MEDLINE]
PMCID:
PMC4146671
[Available on 2015-09-19]
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