Affordable Access

deepdyve-link
Publisher Website

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

Authors
  • Tong, Shengqiang1
  • Shen, Mangmang2
  • Cheng, Dongping2
  • Zhang, Yamei2
  • Ito, Yoichiro3
  • Yan, Jizhong4
  • 1 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. , (China)
  • 2 College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China. , (China)
  • 3 Laboratory of Bioseparation Technologies, Biochemistry and Biophysics Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Bethesda, MD 20892, USA. Electronic address: [email protected]
  • 4 College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China. Electronic address: [email protected] , (China)
Type
Published Article
Journal
Journal of chromatography. A
Publication Date
Sep 19, 2014
Volume
1360
Pages
110–118
Identifiers
DOI: 10.1016/j.chroma.2014.07.057
PMID: 25087742
Source
Medline
Keywords
License
Unknown

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.

Report this publication

Statistics

Seen <100 times