超临界流体色谱与高效液相色谱分离手性化合物的比较

引用本文: 张晶, 陈晓东, 李丽群, 贺建峰, 范军, 章伟光. 超临界流体色谱与高效液相色谱分离手性化合物的比较[J]. 色谱, 2016, 34(3): 321-326. doi: 10.3724/SP.J.1123.2015.11025 shu

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

超临界流体色谱与高效液相色谱分离手性化合物的比较

张晶 ^1, ,
陈晓东 ^2, ,
李丽群 ^1, ,
贺建峰 ^1, ,
范军 ^{1,
,} ,
章伟光 ^{1,2,
,}

1.
1. 华南师范大学化学与环境学院, 广东广州 510006;
2.
2. 广州研创生物技术发展有限公司, 广东广州 510663

通讯作者: 章伟光,范军; 章伟光,范军

基金项目:
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)

摘要: 超临界流体色谱(SFC)分离具有速度快、分离效率高、溶剂消耗少等优点,近年来在手性化合物的分离分析中得到诸多应用。本文对比研究了涂覆型多糖手性色谱柱在SFC和高效液相色谱(HPLC)上拆分24种手性化合物的差异。通过比较这些化合物在色谱柱上的保留时间和选择因子等发现多数化合物在SFC上的分离效率要高于其在HPLC上的分离效率,但HPLC对轴手性化合物的分离效率要优于SFC。SFC和HPLC的分离表现出一定的互补性,随着苯环侧链烷基的碳数增加,化合物在SFC上的保留逐渐增强,而在HPLC的保留却逐渐减弱。叶菌唑在使用SFC和HPLC分析时出现了洗脱顺序反转的现象。这些结果为SFC手性拆分提供了参考。

关键词:

English

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

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: 章伟光,范军; 章伟光,范军

Received Date: 14 November 2015
Fund Project:
国家自然科学基金项目(21171059,21571070)

科技型中小企业技术创新基金项目(13C26214404534)

广东省科技计划项目(2012B010900043,2014A010101145)

广州市科技计划项目(2013J4400027,201508020093).

Abstract: 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.

Key words:

supercritical fluid chromatography (SFC)
/ high performance liquid chromatography (HPLC)
/ polysaccharide-based chiral stationary phases
/ enantioseparation
/ elution order reversal
/ enantiomers

1. [1] Maftouh M, Granier-Loyaux C, Chavana E, et al. J Chromatogr A, 2005, 1088: 67 [1] Maftouh M, Granier-Loyaux C, Chavana E, et al. J Chromatogr A, 2005, 1088: 67
2. [2] Schaffrath M, Weidmann V, Maison W. J Chromatogr A, 2014, 1363: 270 [2] Schaffrath M, Weidmann V, Maison W. J Chromatogr A, 2014, 1363: 270
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 [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] Galea C, Mangelings D, Heyden Y V. Anal Chim Acta, 2015, 886: 1 [4] Galea C, Mangelings D, Heyden Y V. Anal Chim Acta, 2015, 886: 1
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 [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] Nogle L M, Mann C W, Watts W L Jr, et al. J Pharmaceut Biomed Anal, 2006, 40(3): 901[6] Nogle L M, Mann C W, Watts W L Jr, et al. J Pharmaceut Biomed Anal, 2006, 40(3): 901
7. [7] Payagala T, Wanigasekara E, Armstrong D W. Anal Bioanal Chem, 2011, 399(7): 2445 [7] Payagala T, Wanigasekara E, Armstrong D W. Anal Bioanal Chem, 2011, 399(7): 2445
8. [8] Mourier P A, Eliot E, Caude M H, et al. Anal Chem, 1985, 57(14): 2819 [8] Mourier P A, Eliot E, Caude M H, et al. Anal Chem, 1985, 57(14): 2819
9. [9] Guiochon G, Tarafder A. J Chromatogr A, 2011, 1218: 1037 [9] Guiochon G, Tarafder A. J Chromatogr A, 2011, 1218: 1037
10. [10] Novell A, Méndez A, Minguillón C. J Chromatogr A, 2015, 1403: 138 [10] Novell A, Méndez A, Minguillón C. J Chromatogr A, 2015, 1403: 138
11. [11] Lin C, Luo W J, Zhang S, et al. J Sep Sci, 2010, 33(11): 1558 [11] Lin C, Luo W J, Zhang S, et al. J Sep Sci, 2010, 33(11): 1558
12. [12] Nelander H, Andersson S, Öhlén K. J Chromatogr A, 2011, 1218: 9397 [12] Nelander H, Andersson S, Öhlén K. J Chromatogr A, 2011, 1218: 9397
13. [13] Lin C, Liu W N, Fan J, et al. J Chromatogr A, 2013, 1283: 68 [13] Lin C, Liu W N, Fan J, et al. J Chromatogr A, 2013, 1283: 68
14. [14] Yao B X, Liu G Q, Kang S S, et al. Chromatographia, 2011, 74 (7/8): 625[14] Yao B X, Liu G Q, Kang S S, et al. Chromatographia, 2011, 74 (7/8): 625
15. [15] Zhao Y Q, Pritts W A, Zhang S H. J Chromatogr A, 2008, 1189: 245 [15] Zhao Y Q, Pritts W A, Zhang S H. J Chromatogr A, 2008, 1189: 245
16. [16] Matarashvili I, Chankvetadze L, Fanali S, et al. J Sep Sci, 2013, 36(1): 140 [16] Matarashvili I, Chankvetadze L, Fanali S, et al. J Sep Sci, 2013, 36(1): 140
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 [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] Lin C, Fan J, Liu W N, et al. J Pharm Biomed Anal, 2014, 98: 221 [18] Lin C, Fan J, Liu W N, et al. J Pharm Biomed Anal, 2014, 98: 221

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超临界流体色谱与高效液相色谱分离手性化合物的比较

通讯作者: 章伟光,范军; 章伟光,范军

English

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

Corresponding author: 章伟光,范军; 章伟光,范军

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

超临界流体色谱与高效液相色谱分离手性化合物的比较

通讯作者: 章伟光,范军; 章伟光,范军

English

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

Corresponding author: 章伟光,范军; 章伟光,范军

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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