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
1. [1]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
2. [2]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
3. [3]
  Siming Bian , Sijie Luo , Junjie Ou . Application of van Deemter Equation in Instrumental Analysis Teaching: A New Type of Core-Shell Stationary Phase. University Chemistry, 2025, 40(3): 381-386. doi: 10.12461/PKU.DXHX202406087
4. [4]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
5. [5]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
8. [8]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
11. [11]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
12. [12]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
13. [13]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
14. [14]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
15. [15]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
16. [16]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
17. [17]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
18. [18]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
19. [19]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
20. [20]
  Yumiao Gao , Yixin Chen , Jiaxin Wei , Junjie Yu , Yunxia Wang . Guarding the Kingdom: Skin Allies with Sunscreen for Mutual Protection. University Chemistry, 2024, 39(9): 74-80. doi: 10.12461/PKU.DXHX202404149

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(725)
HTML views(132)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142