Citation: ZHANG Jing, CHEN Xiaodong, LI Liqun, HE Jianfeng, FAN Jun, ZHANG Weiguang. Comparative separation of chiral compounds by supercritical fluid chromatography and high performance liquid chromatography[J]. Chinese Journal of Chromatography, ;2016, 34(3): 321-326. doi: 10.3724/SP.J.1123.2015.11025 shu

Comparative separation of chiral compounds by supercritical fluid chromatography and high performance liquid chromatography

ZHANG Jing ¹ ,
CHEN Xiaodong ² ,
LI Liqun ¹ ,
HE Jianfeng ¹ ,
FAN Jun ^1,, ,
ZHANG Weiguang ^1,2,,

1.
1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China;
2.
2. Guangzhou Research & Creativity Biotechnology Co. Ltd., Guangzhou 510663, China

Corresponding author: FAN Jun, ZHANG Weiguang,
Received Date: 14 November 2015

Fund Project: 国家自然科学基金项目(21171059,21571070) (21171059,21571070)科技型中小企业技术创新基金项目(13C26214404534) (13C26214404534)广东省科技计划项目(2012B010900043,2014A010101145) (2012B010900043,2014A010101145)广州市科技计划项目(2013J4400027,201508020093). (2013J4400027,201508020093)

Supercritical fluid chromatographic (SFC) technique has been widely applied in the analysis, determinations and chromatographic preparations of chiral compounds in past decades due to some advantages such as fast speed, high efficiency and low consumption of organic solvents. Herein, 24 kinds of chiral compounds (H1-H24) have been resolved on four polysaccharide-coated chiral stationary phases (CSPs) by SFC and high performance liquid chromatography (HPLC), separately. Taking into account their retention times and selection factors of these compounds, SFC separation showed a better efficiency than HPLC for most of the compounds, except for some axis-chiral compounds. Some complementarity between SFC and HPLC separations was observed. For H15-H17, their retentions in SFC separations showed a strengthening trend with increasing carbon numbers of side alkyl chain, whereas a reverse tendency in HPLC separation was displayed. Most interestingly, an elution order reversal of metconazole enantiomers was found in this work. In brief, these results would provide some valuable references for the development of SFC separation methods in the future.
1. [1]
  [1] Maftouh M, Granier-Loyaux C, Chavana E, et al. J Chromatogr A, 2005, 1088: 67
2. [2]
  [2] Schaffrath M, Weidmann V, Maison W. J Chromatogr A, 2014, 1363: 270
3. [3]
  [3] Xu X F, Shen A J, Guo Z M, et al. Chinese Journal of Chromatography, 2013, 31(3): 185 徐雪峰, 沈爱金, 郭志谋, 等. 色谱, 2013, 31(3): 185
4. [4]
  [4] Galea C, Mangelings D, Heyden Y V. Anal Chim Acta, 2015, 886: 1
5. [5]
  [5] Li Z Y, Fu Q, Li K Y, et al. Chinese Journal of Chromatography, 2014, 32(5): 506 李振宇, 傅青, 李奎永, 等. 色谱, 2014, 32(5): 506
6. [6]
  [6] Nogle L M, Mann C W, Watts W L Jr, et al. J Pharmaceut Biomed Anal, 2006, 40(3): 901
7. [7]
  [7] Payagala T, Wanigasekara E, Armstrong D W. Anal Bioanal Chem, 2011, 399(7): 2445
8. [8]
  [8] Mourier P A, Eliot E, Caude M H, et al. Anal Chem, 1985, 57(14): 2819
9. [9]
  [9] Guiochon G, Tarafder A. J Chromatogr A, 2011, 1218: 1037
10. [10]
  [10] Novell A, Méndez A, Minguillón C. J Chromatogr A, 2015, 1403: 138
11. [11]
  [11] Lin C, Luo W J, Zhang S, et al. J Sep Sci, 2010, 33(11): 1558
12. [12]
  [12] Nelander H, Andersson S, Öhlén K. J Chromatogr A, 2011, 1218: 9397
13. [13]
  [13] Lin C, Liu W N, Fan J, et al. J Chromatogr A, 2013, 1283: 68
14. [14]
  [14] Yao B X, Liu G Q, Kang S S, et al. Chromatographia, 2011, 74 (7/8): 625
15. [15]
  [15] Zhao Y Q, Pritts W A, Zhang S H. J Chromatogr A, 2008, 1189: 245
16. [16]
  [16] Matarashvili I, Chankvetadze L, Fanali S, et al. J Sep Sci, 2013, 36(1): 140
17. [17]
  [17] Tu H S, Fan J, Tan Y, et al. Chinese Journal of Chromatography, 2014, 32(5): 452 涂鸿盛, 范军, 谭艺, 等. 色谱, 2014, 32(5): 452
18. [18]
  [18] Lin C, Fan J, Liu W N, et al. J Pharm Biomed Anal, 2014, 98: 221
1. [1]
  Tong Wang , Liangyu Hu , Shiqi Chen , Xinqiang Fu , Rui Wang , Kun Li , Shuangyan Huan . Determination of Benzenediol Isomers in Cosmetics Using High-Performance Liquid Chromatography Empowered by “Mathematical Separation”. University Chemistry, 2026, 41(1): 9-19. doi: 10.12461/PKU.DXHX202503128
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]
  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
4. [4]
  Yifan Xie , Liyun Yao , Ruolin Yang , Yuxing Cai , Yujie Jin , Ning Li . Exploration and Practice of Online and Offline Hybrid Teaching Mode in High-Performance Liquid Chromatography Experiment. University Chemistry, 2025, 40(11): 100-107. doi: 10.12461/PKU.DXHX202412133
5. [5]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
6. [6]
  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
7. [7]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059
8. [8]
  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
9. [9]
  Gengjia Chen , Junjie Ou . Application of the van Deemter Equation in Instrumental Analysis Teaching: A Case of Organic Polymer Monolithic Columns. University Chemistry, 2025, 40(11): 362-368. doi: 10.12461/PKU.DXHX202502003
10. [10]
  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
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]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
13. [13]
  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
14. [14]
  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
15. [15]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
16. [16]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
17. [17]
  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
18. [18]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(912)
HTML views(206)

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