逆流色谱法手性分离D,L-α-苯甘氨酸
Chiral Separation of D,L-α-Phenylglycine by Countercurrent Chromatography
摘 要
以(D)-(+)-樟脑-10-磺酸作为手性选择剂,运用逆流色谱技术对苯甘氨酸对映异构体进行手性分离。以正己烷-乙酸乙酯-甲醇-水(1+5+1+5)溶液作为两相溶剂系统,手性选择剂在上相中的浓度为258 mmol·L-1,可在2 h内一次性实现10 mg苯甘氨酸的手性分离,分离效果通过手性液相色谱获得验证。
手性分离
D,L-α-苯甘氨酸
(D)-(+)-樟脑-10-磺酸
Countercurrent chromatography
Chiral separation
D,L-α-Phenylglycine
D-(+)-10-camphorsulfonic acid
Abstract
Countercurrent chromatography was applied for chiral separation of D,L-α-phenylglycine using D-(+)-10-camphorsulfonic acid as a chiral selector. The separation was performed with a two-phase solvent system composed of n-hexane, ethyl acetate, methanol and water. The upper phase contained 258 mmol·L-1 of chiral selector. The maximum amount of sample separated within 2 hours in a one-time injection was up to 10 mg. The separation results were confirmed by chiral LC method.
中图分类号 O652.6
所属栏目 工作简报
基金项目 云南省教育厅科学研究基金项目(2013Y108)
收稿日期 2014/4/8
修改稿日期
网络出版日期
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备注吕迎春(1973-),女,云南普洱人,副教授,硕士研究生,主要研究方向手性分离。
引用该论文: LV Ying-chun,FAN Zhu-qing,HOU Yun-hong,SHANG Yu-nan. Chiral Separation of D,L-α-Phenylglycine by Countercurrent Chromatography[J]. Physical Testing and Chemical Analysis part B:Chemical Analysis, 2015, 51(4): 454～457
吕迎春,樊竹青,侯云洪,尚宇南. 逆流色谱法手性分离D,L-α-苯甘氨酸[J]. 理化检验－化学分册, 2015, 51(4): 454～457
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参考文献
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【9】TONG Sheng-qiang, GUAN Yi-xin, YAN Ji-zhong, et al. Enantiomeric separation of (R,S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector［J］. Journal of Chromatography A, 2011,1218(33):5602-5608.
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【11】DURET P, FOUCAULT A, MARGRAFF R. Vancomycin as a chiral selector in centrifugal partition chromatography［J］. Journal of Liquid Chromatography & Related Technologies, 2000,23(2):295-312.
【12】CAI Ying, YAN Zhi-hong, ZI Min, et al. Preparative enantioseparation of DL-α-methylbenzylamine by high-speed countercurrent chromatography using L-(1)-tartaric acid as chiral selector［J］. Journal of Liquid Chromatography & Related Technologies, 2007,30(9/10):1489-1495.
【13】LV Ying-chun, YAN Zhi-hong, MA Chao, et al. Preparative Enantioseparation of ofloxacin by high-speed countercurrent chromatography using L-(+)-tartaric acid as chiral selectors［J］. Journal of Liquid Chromatography & Related Technologies, 2010,33(13):1328-1334.
【14】TONG Sheng-qiang, YAN Ji-zhong, GUAN Yi-xin, et al. Separation of α-cyclohexylmandelic acid enantiomers by biphasic chiral recognition high speed counter-current chromatography［J］. Journal of Chromatography A, 2010,1217(18):3044-3052.
【2】DOMON B, HOSTETTMANN K, KOVACEVIC K, et al. Separation of the enantiomers of (±)-norephedrine by rotation locular counter-current chromatography［J］. Chromatographia, 1982,250(26):149-151.
【3】TAKEUCHI T, HORIKAWA R, TANIMURA T. Complete resolution of D,L-isoleucine by droplet counter-current chromatography［J］. Chromatographia, 1984,284(1):285-288.
【4】MA Ying, ITO Y, BERTHOD A. A chromatographic method for measuring KF of enantiomer-chiral selector complexes［J］. Journal of Liquid Chromatography & Related Technologies, 1999,22(19):2945-2955.
【5】DELGADO B, PEREZ E, SATANO M C, et al. Enantiomer separation by counter-current chromatography: optimisation and drawbacks in the use of L-proline derivatives as chiral selectors［J］. Journal of Chromatography A, 2005,1092(1):36-42.
【6】YUAN Li-ming, LIU Jia-chuan, YAN Zhi-hong, et al. Enantioseparation of chlorpheniramine by high speed countercurrent chromatography using carboxymethyl-β-cyclodextrin as chiral selector［J］. Journal of Liquid Chromatography & Related Technologies, 2005,28(19):3057-3063.
【7】AI Ping, LIU Jia-chuan, ZI Min, et al. Enantioseparation of aminoglutethimide by high-speed counter-current chromatography using carboxymethly-β-cyclodextrin as chiral selector［J］. Chinese Chemical Letters, 2006,17(6):787-790.
【8】TONG Sheng-qiang, YAN Ji-zhong, GUAN Yi-xin. Preparative separation of isomeric caffeoylquinic acid from flos lonicerae by pH-zone-refining counter-current chromatography［J］. Journal of Chromatography A, 2008,1212(1/2):48-53.
【9】TONG Sheng-qiang, GUAN Yi-xin, YAN Ji-zhong, et al. Enantiomeric separation of (R,S)-naproxen by recycling high speed counter-current chromatography with hydroxypropyl-β-cyclodextrin as chiral selector［J］. Journal of Chromatography A, 2011,1218(33):5602-5608.
【10】GAVIOLI E, MAIER N M, MINGUILLON C, et al. Preparative enantiomer separation of dichlorprop with a cinchona-derived dhiral selector employing centrifugal partition chromatography and high-performance liquid chromatography: A comparative study［J］. Analytical Chemistry, 2004,76(17):5837-5848.
【11】DURET P, FOUCAULT A, MARGRAFF R. Vancomycin as a chiral selector in centrifugal partition chromatography［J］. Journal of Liquid Chromatography & Related Technologies, 2000,23(2):295-312.
【12】CAI Ying, YAN Zhi-hong, ZI Min, et al. Preparative enantioseparation of DL-α-methylbenzylamine by high-speed countercurrent chromatography using L-(1)-tartaric acid as chiral selector［J］. Journal of Liquid Chromatography & Related Technologies, 2007,30(9/10):1489-1495.
【13】LV Ying-chun, YAN Zhi-hong, MA Chao, et al. Preparative Enantioseparation of ofloxacin by high-speed countercurrent chromatography using L-(+)-tartaric acid as chiral selectors［J］. Journal of Liquid Chromatography & Related Technologies, 2010,33(13):1328-1334.
【14】TONG Sheng-qiang, YAN Ji-zhong, GUAN Yi-xin, et al. Separation of α-cyclohexylmandelic acid enantiomers by biphasic chiral recognition high speed counter-current chromatography［J］. Journal of Chromatography A, 2010,1217(18):3044-3052.
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