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.

Two-Dimensional Transport Dispersive Model for Separating Glycolic Acid and NaCl with Ligand Exchange Chromatography

“…Ligand exchange chromatography, a kind of separation method with low energy consumption and high efficiency, can purify organic acids and also be used in the separation of GA. This method is based on the difference in interaction force between separation medium and components, shows a good selectivity and separation effect, and is widely used in the separation of sugar, amino acids, and natural substances. , For example, 3-phenyllactic and mandelic acids and phenylalanine could be efficiently separated with ligand exchange chromatography. For that separation method, the preparation of a separation medium, , the effect of process parameter, the process modeling, and process amplification are the main concerns.…”

Preparative enantioseparation of loxoprofen precursor by recycling countercurrent chromatography with hydroxypropyl‐β‐cyclodextrin as a chiral selector

“…Therefore, it is of great significance for the anti-inflammatory drug loxoprofen to establish an efficient method for resolution Countercurrent chromatography is a liquid-liquid partition chromatography using no solid support for the stationary phase without irreversible absorption involved during separation, and it has been widely used for preparative separation of active components from natural products [9,10]. In the recent five years, increasing number of literatures reporting chiral separation of intermediates/drugs by countercurrent chromatography with miscellaneous chiral selectors has been published [11][12][13][14][15][16][17][18]. However, it is still difficult to achieve a successful enantioseparation by modern countercurrent chromatographic technique due to its low separation efficiency, i.e., much lower theoretical plates of separation column of countercurrent chromatography than conventional LC was found [19][20][21].…”

Application of pH‐zone‐refining countercurrent chromatography in the chiral separation of two β‐adrenergic blocking agents

“…Compared with traditional liquid chromatographic techniques, much smaller number of literatures about chiral separation by countercurrent chromatography was available due to its relatively low theoretical plates of separation column [20][21][22][23]. However, in the recent two years, increasing number of papers has been published on preparative enantioseparation by countercurrent chromatography [24][25][26][27][28][29][30][31][32][33]. Unfortunately, only five papers reporting successful chiral separations could be found in the literature when it comes to pH-zone-refining countercurrent chromatography since 1990s [34][35][36][37][38].…”