Citation: LIN Xiaojian, GONG Rujin, LI Ping, YU Jianguo. Chromatographic separation of aminoglutethimide enantiomers on cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase[J]. Chinese Journal of Chromatography, ;2014, 32(8): 880-885. doi: 10.3724/SP.J.1123.2014.04022 shu

Chromatographic separation of aminoglutethimide enantiomers on cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase

1.
School of Chemical Engineering, East China University of Science and Technology, State Key Laboratory of Chemical Engineering, Shanghai 200237, China

Corresponding author: LI Ping,
Received Date: 14 April 2014
Available Online: 4 June 2014
Fund Project: 国家自然科学基金项目(21276080). (21276080)

Aminoglutethimide (AG) has been used clinically as a drug in the treatment of hormone-dependent metastatic breast cancer. It was reported that S-(-)-AG enantiomer had small activity and sometimes might cause side effects. Therefore, it was of great significance to obtain the high-purity R-(+)-AG by enantioseparation. In this work, aminoglutethimide enantiomers were separated by high performance liquid chromatography (HPLC) using an analytical column which was packed with cellulose tris(3,5-dimethylphenylcarbamate) stationary phase (Chiralcel OD-H). The solubilities of racemic AG in two different solvent compositions, n-hexane/ethanol and n-hexane/isopropanol, were measured, separately. The effects of alcohol content and monoethanolamine additive on the separation performance of racemic AG by HPLC were investigated. According to the experiments, n-hexane-ethanol (30:70, v/v) with 0.1% monoethanolamine additive was selected as the mobile phase. The separation factor, resolution, asymmetry factor, number of theoretical plates and maximum column capacity were measured and analyzed for the chromatographic separation of racemic AG at a flow-rate of 0.6 mL/min and column temperature of 25-40℃, with Chiralcel OD-H as stationary phase and n-hexane-ethanol (30:70, v/v) with 0.1% monoethanolamine as mobile phase. This work provides the basic information of chromatographic separation for the batch and continuous production of aminoglutethimide enantiomers.
- high performance liquid chromatography (HPLC),
- chiral stationary phase,
- chiral resolution,
- aminoglutethimide
1. [1]
  [1] Elbashir A A, Suliman F E O, Saad B, et al. Talanta, 2009, 77(4): 1388
2. [2]
  [2] Lu D Q, Li Y L, Ling X Q, et al. Lishizhen Medicine and Materia Medica Research (卢定强, 李衍亮, 凌岫泉, 等. 时珍国医国药), 2009, 20(7): 1731
3. [3]
  [3] Huang B, Yang L R, Wu J P. Chemical Industry and Engineering Progress (黄蓓, 杨立荣, 吴坚平. 化工进展), 2002, 21(6): 375
4. [4]
  [4] Wang M. Chinese Journal of Chromatography (王敏. 色谱), 2014, 32(2): 198
5. [5]
  [5] Wang L P, Fan H J, Wu K H, et al. Chinese Journal of Chromatography (王李平, 范华均, 巫坤宏, 等. 色谱), 2012, 30(12): 1265
6. [6]
  [6] Lee E, Park M B, Kim J M, et al. Korean J Chem Eng, 2010, 27(1): 231
7. [7]
  [7] Ali I, Naim L, Ghanem A, et al. Talanta, 2006, 69(4): 1013
8. [8]
  [8] Aboul-Enein H Y, Serignese V. Chirality, 1994, 6(5): 378
9. [9]
  [9] Aboul-Enein H Y, Serignese V. Chirality, 1998, 10(4): 358
10. [10]
  [10] Gong R, Li P, Yu J G. J Chromatogr A, 2013, 1286: 119
11. [11]
  [11] Mao S, Zhang Y, Rohani S, et al. J Sep Sci, 2012, 35(17): 2273
12. [12]
  [12] Du X, Wang Q, He X. Chemical Reagents (杜曦, 王钦, 何晓. 化学试剂), 2011, 33(7): 652
13. [13]
  [13] Ribeiro A E, Graca N S, Pais L S, et al. Sep Pur Technol, 2008, 61(3): 375
14. [14]
  [14] Arnell R, Forssén P, Fornstedt T, et al. J Chromatogr A, 2009, 1216(16): 3480
15. [15]
  [15] Patil N S, Mendhe R B, Sankar A A, et al. J Chromatogr A, 2008, 1177(2): 234
16. [16]
  [16] Kusters E, Spondlin C. J Chromatogr A, 1996, 737(2): 333
17. [17]
  [17] Ellington J J, Evans J J, Prickett K B, et al. J Chromatogr A, 2001, 928(2): 145
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