Enantioseparation and molecular modeling study of five β‐adrenergic blockers on Chiralpak IC column

Abstract

A new high‐performance liquid chromatography (HPLC) method was developed for the enantiomeric resolution of five β‐adrenergic blockers on a Chiralpak IC column (250 mm × 4.6 mm, 5.0 μm particle size) in normal phase mode. The mobile phase used was n‐hexane‐ethanol‐diethylamine in different proportions at the flow rate of 1.0 mL/min with the column temperature of 25°C using a UV detector at 230 nm. The influences of base additives and alcohol modifiers were evaluated and optimized. The maximum resolution values for bevantolol, propranolol carteolol, esmolol, and metoprolol were 4.80, 2.77, 2.09, 2.30, and 1.11, respectively. To gain a better understanding of the interaction between chiral stationary phase and analyte enantiomers, the molecular docking of chiral stationary phase with five pairs of enantiomer was carried out using AutoDock molecular docking technique. By simulation studies, the mechanism of chiral recognition was determined. According to the results, hydrogen bond interactions and π‐π interactions were the chief interactions for the chiral recognition.

Modelling approaches for chiral chromatography on polysaccharide-based and macrocyclic antibiotic chiral selectors: A review

“…Zhao et al [57] performed docking calculations on a CDCPC CSP using five beta blockers. Different enantioselectivity values were experimentally seen for these analytes and the study sought to rationalize this with docking calculations.…”

Enantioseparation and molecular modeling study of chiral amines as three naphthaldimine derivatives using amylose or cellulose trisphenylcarbamate chiral stationary phases

“…In cellulose tris(3,5‐dimethylphenylcarbamate) chiral selector, chiral cavities are created between the sheets formed by the polymer chains near the carbohydrate backbone, which incorporate various levels of chiral information 29,33–35 . Enhanced chiral discrimination of a chiral molecule occurs if the ligand (enantiomer) is an appropriate fit to the chiral cavities of the CSP (receptor) 35 . Fitting of the enantiomers was stabilized by the diverse interactions that occur during the chiral separation process 23 .…”

“…In cellulose tris(3,-5-dimethylphenylcarbamate) chiral selector, chiral cavities are created between the sheets formed by the polymer chains near the carbohydrate backbone, which incorporate various levels of chiral information. 29,[33][34][35] Enhanced chiral discrimination of a chiral molecule occurs if the ligand (enantiomer) is an appropriate fit to the chiral cavities of the CSP (receptor). 35 that occur during the chiral separation process.…”

“…29,[33][34][35] Enhanced chiral discrimination of a chiral molecule occurs if the ligand (enantiomer) is an appropriate fit to the chiral cavities of the CSP (receptor). 35 that occur during the chiral separation process. 23 Table 7 and Figure 3 show the molecular modeling data and representative interactions of six complexes [(S)-and (R)leucinol as 1-naphthaldimine, 2-naphthaldimine and 2-hydroxynaphthaldimine derivatives] with the receptor cellulose tris (3,5-dimethylphenylcarbamate).…”

Enantioseparation and molecular modeling study of eight psychoactive drugs on a coated polysaccharide‐based chiral stationary phase

“…By carrying out a molecular docking, the binding energy, the number and strength of intermolecular interactions between the analyte and CSP are available, which will be helpful to precisely elucidate the chiral recognition process [30]. For example, Zhao et al have carried out the molecular docking to study the enantioseparation of five β-adrenergic blockers on a Chiralpak IC column, and found that hydrogen bond and π-π interactions were the chief interactions for the chiral recognition [31]. Therefore, the molecular docking method was determined in this article to investigate the chiral separation mechanisms of cellulose tris(4-methylbenzoate) CSP, and then docking mechanisms of eight psychoactive drugs were elaborated.…”