Mechanism of Resolution of Enantiomers of Lomefloxacin on Chiralcel OJ Column
摘 要
提出了洛美沙星对映体的高效液相色谱拆分方法。选用Chiralcel OJ手性柱,正己烷-异丁醇(90+10)的混合溶液为流动相,流量为0.6 mL·min-1,柱温为30 ℃,检测波长为287 nm。通过溶质计量置换保留模型和热力学理论对Chiralcel OJ手性柱拆分机理进行了探讨。结果表明:保留时间较短的洛美沙星对映体的lgI值和Z值均小于保留时间较长的对映体。在试验的温度范围内,用lnα对1/T作图,得到Van′t Hoff曲线呈线性关系,焓变和熵变之差为负值,说明手性拆分过程为焓控过程。
Abstract
Resolution of enantiomers of lomefloxacin by HPLC was proposed using the Chiralcel OJ column as stationary phase with column temperature of 30 ℃, and a mixture of n-hexane and iso-butanol (90+10) as mobile phase with a flow-rate of 0.6 mL·min-1. UV-detection at the wavelength of 287 nm was adopted in the determination. Based on the solute stoichiometric displacement model of retention and the thermodynamic theory, mechanism of resolution of enantiomers of lomefloxacin on this chiral column was studied. It was found that values of lgI and Z of the enantiomer with shorter retention time were smaller than that of the enantiomer with longer retention time. Good linearity of the Van′t Hoff curve was obtained when plotting lnα vs. 1/T, within the testing temperature range; and the difference between enthalpy change and entropy change was shown to be a negative value. It was thus illustrated that the chiral resolution of the enantiomers was an enthalpy-controlled process.
中图分类号 O652.62
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基金项目 辽宁省教育厅创新团队项目(2008T093);辽宁科技大学青年基金团队项目子课题(2010T06);辽宁科技大学大学生科研训练项目(第六期)
收稿日期 2010/12/9
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备注唐晓丹(1979-),女,辽宁盘锦人,硕士,讲师,研究方向为天然药物中间体及手性药物分离。
引用该论文: TANG Xiao-dan,ZHANG Yan,JIA Hong-min,CONG Jing-xiang,TIAN Yu2. Mechanism of Resolution of Enantiomers of Lomefloxacin on Chiralcel OJ Column[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2011, 47(7): 764~767
唐晓丹,张燕,贾宏敏,丛景香,田雨. 洛美沙星对映体在Chiralcel OJ柱上的拆分机理[J]. 理化检验-化学分册, 2011, 47(7): 764~767
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【3】韦寿莲,严子军,戚利华.毛细管电泳手性拆分喹诺酮类药物对映体[J].理化检验-化学分册, 2009,45(6):714-716.
【4】FOSTER R T, CARR R A, PASUTTO F M, et al. Sterespecific high-performance liquid chromatographic assay of lomefloxacin in hurman plasma[J]. J Pharm Biomed Anal, 1995,13(12):1243-1248.
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【6】楼张英,黄一平.氟喹诺酮类药物的手性拆分研究进展[J].医药导报, 2004,23(11):844-846.
【7】RADHAKRISHNA T, RAO D S, VVAS K, et al. Enantiomeric separation of a moxifloxacin intermediate by chiral liquid chromatography using cellulose based stationary phases[J]. J Pharm Biomed Anal, 2000,22(4):691-697.
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【10】GENG X D, REGNIER F E. Stoichiometric displacement of solvent by nonpolar solutes in reverse-phase liquid chromatography[J]. J Chromatogr, 1985,332:147-168.
【11】PERSSON B A, ANDERSSON S. Unusual effects of separation conditions on chiral separations[J]. J Chromatogr A, 2001,906:195-203.
【12】VOLKER S. Practice and theory of enantioselective complexation gas chromatography[J]. J Chromatogr A, 2002,965:315-356.
【13】STRINGHAM R W, BLACKWELL J A. Factors that control successful entropically driven chiral separations in SFC and HPLC[J]. Anal Chem, 1997,69(7):1414-1420.
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