Enantioseparation of 3‐phenyllactic acid by chiral ligand exchange countercurrent chromatography. Issue 8 (21st March 2017)

• Record Type: Journal Article
• Authors: Tong, Shengqiang; Wang, Xiaoping; Shen, Mangmang; Lv, Liqiong; Lu, Mengxia; Bu, Zhisi; Yan, Jizhong
• Is Part Of: Journal of separation science. Volume 40:Issue 8(2017)
• Page Start: 1834
• Page End: 1842
• Publication Date: 2017-03-21
• Subjects: chiral ligand exchange -- countercurrent chromatography -- enantioseparation -- 3‐phenyllactic acid; Separation (Technology) -- Periodicals; Chromatographic analysis -- Periodicals; 543.089
• DOI: 10.1002/jssc.201601384
• Languages: English
• ISSNs: 1615-9306

Abstract

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.