Fang Zhili, Guo Ziyuan, Qin Qing, Fan Jun, Yin Yong, Zhang Weiguang
Institute of Special Materials/School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China.
J Chromatogr Sci. 2013 Feb;51(2):133-7. doi: 10.1093/chromsci/bms117. Epub 2012 Jul 19.
A direct semi-preparative high performance liquid chromatography (HPLC) enantioseparation of ofloxacin was performed on chemically immobilized cyclodextrin derivative-mono (6A-azido-6A-deoxy)-per(p-chlorophenyl carbamoylated) β-CD chiral stationary phase. Conditions for semi-preparative separations were established using a 250 × 4.6 mm i.d. column and subsequently extended to a 250 × 10.0 mm i.d. column that enabled separations on a milligram scale. Optimization of the chromatographic conditions (mobile phase and column load) with respect to better efficiency, resolution and peak retention resulted in a system capable of separating up to 304 mg of (-)-(S)-ofloxacin and 56 mg of (+)-(R)-ofloxacin of the racemate over 6 h. The purities of the separated enantiomers were determined by HPLC. Moreover, both separated enantiomers were characterized by mass spectrometry; then, the absolute configuration of the products was clearly confirmed by polarimetry.
在化学固定化环糊精衍生物 - 单（6A - 叠氮基 - 6A - 脱氧） - 全（对氯苯基氨基甲酰化）β - CD手性固定相上进行了氧氟沙星的直接半制备高效液相色谱（HPLC）对映体分离。使用内径为250×4.6 mm的色谱柱建立了半制备分离条件，随后扩展到内径为250×10.0 mm的色谱柱，该色谱柱能够进行毫克级的分离。通过优化色谱条件（流动相和柱负载量）以提高效率、分辨率和峰保留率，得到了一个能够在6小时内分离外消旋体中高达304 mg的（ - ） - （S） - 氧氟沙星和56 mg的（ + ） - （R） - 氧氟沙星的系统。通过HPLC测定分离出的对映体的纯度。此外，两种分离出的对映体都通过质谱进行了表征；然后，通过旋光法明确确认了产物的绝对构型。
