Preparation and Application of Isoquinolinecarboxylic Acid Derivative as Chiral Stationary Phase for Ligand Exchange Chromatography
Abstract A novel chiral stationary phase (C 16 -( S )-THIQCA) for ligand exchange high-performance liquid chromatography was prepared by synthesizing 2-(2-hydroxyl) hexadecyl-( S )-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid as a chiral selector and coating it on ODS-bonded stationary phase. The enantiomeric resolutions of 16 D,L -amino acids were achieved on C 16 -( S )-THIQCA by using cupric acetate aqueous solution as mobile phase, column temperature 25°C, and detection at UV 254 nm. The enantioselectivities α of the D,L -amino acids separated were found to be in the range from 1.09 to 1.67 with the resolution R s ranging from 1.0 to 4.8. The elution order of D -isomer before L -isomer was observed for all D,L -amino acids used. The effects of chromatographic conditions including flow rate, column temperature, pH, and the concentration of Cu 2+ and NH 4 + on the resolutions of D,L -amino acid enantiomers were discussed.