title: Enantioseparation and impurity determination of the enantiomers of novel phenylethanolamine derivatives by high performance liquid chromatography on amylose stationary phase.
abstract: Simple and efficient analytical HPLC methods using Chiralpak AS-H as chiral stationary phase were developed for direct enantioseparation of 11 novel phenylethanolamine derivatives. The chromatographic experiments were performed in normal phase mode with n-hexane-ethanol-triethylamine (TEA) as mobile phase. Excellent baseline enantioseparation was obtained for most of compounds. The effects of the concentration of organic modifiers and column temperature were studied for the enantiomeric separation. The mechanism of chiral recognition was discussed based on the relationship between the thermodynamic parameters and structures of compounds. It was found that the enantioseparations were all enthalpy driven, and the tert-butyl groups of compounds had significant influence on the chiral recognition. Trantinterol enantiomers were resolved (R(s)=2.73) within 14 min using n-hexane-ethanol-TEA (98:2:0.1, v/v/v) as mobile phase with a flow rate of 0.8 mL min(-1) at 30 degrees C. The optimized method was validated for linearity, precision, accuracy and stability in solution and proved to be robust. The limits of detection (LOD) and quantification (LOQ) for (+)-trantinterol were 0.15 and 0.46 microg mL(-1). The method was applied for enantiomeric impurity determination of (-)-trantinterol bulk samples.
authors.affiliation: Department of Analytical Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
authors.forename: Jing
authors.initials: J
authors.lastname: Yang
authors.forename: Jin
authors.initials: J
authors.lastname: Guan
authors.forename: Li
authors.initials: L
authors.lastname: Pan
authors.forename: Kun
authors.initials: K
authors.lastname: Jiang
authors.forename: Maosheng
authors.initials: M
authors.lastname: Cheng
authors.forename: Famei
authors.initials: F
authors.lastname: Li
mesh_terms: D000688:Amylose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods*; D004983:Ethanolamines / Q000032:analysis*; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D004983:Ethanolamines; D000688:Amylose