title: Enantioseparation of 3-phenyllactic acid by chiral ligand exchange countercurrent chromatography.
abstract: 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.
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Shengqiang
authors.initials: S
authors.lastname: Tong
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Wang
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Mangmang
authors.initials: M
authors.lastname: Shen
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Liqiong
authors.initials: L
authors.lastname: Lv
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Mengxia
authors.initials: M
authors.lastname: Lu
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Zhisi
authors.initials: Z
authors.lastname: Bu
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Jizhong
authors.initials: J
authors.lastname: Yan
mesh_terms: D000890:Anti-Infective Agents / Q000302:isolation & purification*; D003377:Countercurrent Distribution; D007773:Lactates / Q000302:isolation & purification*; D008024:Ligands; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D007773:Lactates; D008024:Ligands; C017648:3-phenyllactic acid
keywords: 3-phenyllactic acid; chiral ligand exchange; countercurrent chromatography; enantioseparation