Synergetic mechanism and enantioseparation of aromatic β-amino acids by biphasic chiral high-speed counter-current chromatography.
A biphasic chiral recognition system based on chiral ligand exchange with Cu(II)-N-n-dodecyl-L-proline and hydroxypropyl-β-cyclodextrin as an additive was developed to enantioseparate aromatic β-amino acids by high-speed counter-current chromatography. The biphasic chiral recognition system was established with an n-butanol/water (1:1, v/v) solvent system by adding N-n-dodecyl-L-proline and Cu(II) ions to the organic phase and hydroxypropyl-β-cyclodextrin to the aqueous phase. Several separation parameters, such as temperature, pH value, and chiral selector concentration, were systematically investigated by enantioselective liquid-liquid extraction. Under the optimal separation conditions, 54.5 mg of (R,S)-β-phenylalanine and 74.3 mg of (R,S)-β-3,4-dimethoxyphenylalanine were baseline enantioseparated. More importantly, the synergistic enantiorecognition mechanism, based on the Cu(II)-N-n-dodecyl-L-proline and hydroxypropyl-β-cyclodextrin, was discussed for the first time.
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Chao
C
Han
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Jianguang
J
Luo
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Zhongrui
Z
Li
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Yingqi
Y
Zhang
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Huijun
H
Zhao
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China.
Lingyi
L
Kong
D024322:Amino Acids, Aromatic / Q000737:chemistry / Q000302:isolation & purification*; D003377:Countercurrent Distribution; D059625:Liquid-Liquid Extraction; D015394:Molecular Structure; D013237:Stereoisomerism
D024322:Amino Acids, Aromatic
Aromatic beta-amino acid; Biphasic chiral recognition; High-speed counter-current chromatography; Synergetic mechanism