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Enantioseparation of 3‐phenyllactic acid by chiral ligand exchange countercurrent chromatography
Author(s) -
Tong Shengqiang,
Wang Xiaoping,
Shen Mangmang,
Lv Liqiong,
Lu Mengxia,
Bu Zhisi,
Yan Jizhong
Publication year - 2017
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201601384
Subject(s) - chemistry , enantiomer , chromatography , countercurrent chromatography , ligand (biochemistry) , carboxylic acid , chiral ligand , butanol , enantioselective synthesis , high performance liquid chromatography , organic chemistry , ethanol , catalysis , biochemistry , receptor
3‐Phenyllactic acid is an antimicrobial compound with broad‐spectrum activity against various bacteria and fungus. The observed difference in pharmacological activity between optical isomeric 3‐phenyllactic acid necessitates a method for enantioseparation. Chiral ligand exchange countercurrent chromatography was investigated for the enantioseparation of 3‐phenyllactic acid with a synthesized chiral ligand. A two‐phase solvent system was composed of n ‐butanol/hexane/water (0.4:0.6:1, v/v/v) to which N ‐ n ‐dodecyl‐ l ‐hydroxyproline was added to the organic phase as chiral ligand and cupric acetate was added in the aqueous phase as a transitional metal ion. The influence factors were optimized by enantioselective liquid–liquid extraction. Baseline enantioseparation of racemic 3‐phenyllactic acid by analytical high‐speed countercurrent chromatography was achieved. The optical purities of enantiomeric 3‐phenyllactic acid reached 99.0%, as determined by chiral high‐performance liquid chromatography.