Chiral Separation by Ultrafast and Two-Dimensional Liquid Chromatography

doi:10.6023/cjoc202005046

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3794-3801.DOI: 10.6023/cjoc202005046 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

超快速和二维液相色谱手性分离

许瑶, 康经武

中国科学院上海有机化学研究所生命有机化学国家重点实验室上海 200032

收稿日期:2020-05-18 修回日期:2020-06-29 发布日期:2020-07-17
通讯作者: 康经武 E-mail:jingwu.kang@sioc.ac.cn
基金资助:
国家自然科学基金（Nos.21775158，21375140，21175146）资助项目.

Chiral Separation by Ultrafast and Two-Dimensional Liquid Chromatography

Xu Yao, Kang Jingwu

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032

Received:2020-05-18 Revised:2020-06-29 Published:2020-07-17
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21775158, 21375140, 21175146).

Although the chiral separation techniques represented by the polysaccharides-based chiral stationary phases are almost matured, the chiral separation for complex samples remains a challenge. To this end, two dimensional liquid chromatography has been developed rapidly. Recently, to achieve the chiral separation with two dimensional liquid chromatoraphy, the development of the ultrafast liquid chromatography has caused considerable attention. The development of ultrafast liquid chromatography and two-dimensional liquid chromatography also caters to the development of high-throughput organic synthesis technology. In this review the recent progress in the chiral separation by the ultrafast and two-dimensional liquid chromatography is summarized. This review focuses on the progress in the techniques of the chiral packing materials for ultrafast chromatography, the chiral separation strategy and its application in complex samples. Finally, the application perspective of ultra-fast and two-dimensional liquid phase in high-throughput organic synthesis techniques is prospected.

Key words: ultrafast liquid chromatography, two-dimensional liquid chromatography, chiral separation, high-throughput separation

Cite this article

Xu Yao, Kang Jingwu. Chiral Separation by Ultrafast and Two-Dimensional Liquid Chromatography[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3794-3801.

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References

[1] De Camp, W. H. J. Pharm. Biomed. Anal. 1993, 11, 1167.
[2] Maier, N. M.; Franco, P.; Lindner, W. J. Chromatogr. A 2001, 906, 3.
[3] Hegade, R. S.; Lynen, F. J. Chromatogr. A 2019, 1586, 116.
[4] Pirok, B. W. J.; Stoll, D. R.; Schoenmakers, P. J. Anal. Chem. 2019, 91, 240.
[5] Lorenz, H.; Seidel-Morgenstern, A. Angew. Chem., Int. Ed. 2014, 53, 1218.
[6] Regalado, E. L.; Kozlowski, M. C.; Curto, J. M.; Ritter, T.; Campbell, M. G.; Mazzotti, A. R.; Hamper, B. C.; Spilling, C. D.; Mannino, M. P.; Wan, L.; Yu, J. Q.; Liu, J.; Welch, C. J. Org. Biomol. Chem. 2014, 12, 2161.
[7] Major, E. R. LC GC Europe 2012, 25, 1.
[8] Mazzeo, J. R.; Neue, U. D.; Kele, M.; Plumb, R. S. Anal. Chem. 2005, 77, 460 A.
[9] Blue, L. E.; Franklin, E. G.; Godinho, J. M.; Grinias, J. P.; Grinias, K. M.; Lunn, D. B.; Moore, S. M. J. Chromatogr. A 2017, 1523, 17.
[10] MacNair, J. E.; Lewis, K. C.; Jorgenson, J. W. Anal. Chem. 1997, 69, 983.
[11] Jorgenson, J. W. Annu. Rev. Anal. Chem. 2010, 3, 129.
[12] Perera, D.; Tucker, J. W.; Brahmbhatt, S.; Helal, C. J.; Chong, A.; Farrell, W.; Richardson, P.; Sach, N. W. Science 2018, 359, 429.
[13] Robbins, D. W.; Hartwig, J. F. Science 2011, 333, 1423.
[14] Barhate, C. L.; Wahab, M. F.; Tognarelli, D. J.; Berger, T. A.; Armstrong, D. W. Anal. Chem. 2016, 88, 8664.
[15] Ismail, O. H.; Ciogli, A.; Villani, C.; De Martino, M.; Pierini, M.; Cavazzini, A.; Bell, D. S.; Gasparrini, F. J. Chromatogr. A 2016, 1427, 55.
[16] Patel, D. C.; Breitbach, Z. S.; Wahab, M. F.; Barhate, C. L.; Armstrong, D. W. Anal. Chem. 2015, 87, 9137.
[17] Regalado, E. L.; Welch, C. J. J. Sep. Sci. 2015, 38, 2826.
[18] Wahab, M. F.; Wimalasinghe, R. M.; Wang, Y.; Barhate, C. L.; Patel, D. C.; Armstrong, D. W. Anal. Chem. 2016, 88, 8821.
[19] Welch, C. J.; Regalado, E. L. J. Sep. Sci. 2014, 37, 2552.
[20] Kotoni, D.; Ciogli, A.; Molinaro, C.; D'Acquarica, I.; Kocergin, J.; Szczerba, T.; Ritchie, H.; Villani, C.; Gasparrini, F. Anal. Chem. 2012, 84, 6805.
[21] Barhate, C. L.; Wahab, M. F.; Breitbach, Z. S.; Bell, D. S.; Armstrong, D. W. Anal. Chim. Acta 2015, 898, 128.
[22] Ismail, O. H.; Ciogli, A.; Villani, C.; De Martino, M.; Pierini, M.; Cavazzini, A.; Bell, D. S.; Gasparrini, F. J. Chromatogr. A 2016, 1427, 55.
[23] Kirkland, J. J.; Langlois, T. J.; DeStefano, J. J. Am. Lab. 2007, 39, 18.
[24] Gritti, F.; Leonardis, I.; Abia, J.; Guiochon, G. J. Chromatogr. A 2010, 1217, 3819.
[25] Guiochon, G.; Gritti, F. J. Chromatogr. A 2011, 1218, 1915.
[26] Hayes, R.; Ahmed, A.; Edge, T.; Zhang, H. J. Chromatogr. A 2014, 1357, 36.
[27] Jandera, P.; Hájek, T.; Staňková, M. Anal. Bioanal. Chem. 2015, 407, 139.
[28] Tanaka, N.; McCalley, D. V. Anal. Chem. 2016, 88, 279.
[29] Reischl, R. J.; Hartmanova, L.; Carrozzo, M.; Huszar, M.; Fruhauf, P.; Lindner, W. J. Chromatogr. A 2011, 1218, 8379.
[30] Lomsadze, K.; Jibuti, G.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2012, 1234, 50.
[31] Kharaishvili, Q.; Jibuti, G.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2016, 1467, 163.
[32] Berger, T. A. J. Chromatogr. A 2017, 1510, 82.
[33] Bezhitashvili, L.; Bardavelidze, A.; Mskhiladze, A.; Gumustas, M.; Ozkan, S. A.; Volonterio, A.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2018, 1571, 132.
[34] D'Orazio, G.; Kakava, R.; Volonterio, A.; Fanali, S.; Chankvetadze, B. Electrophoresis 2017, 38, 1932.
[35] Mao, X. J.; Li, J.; Liu, D.; Qiao, T.; Ma, L.; Sun, X.; Xu, L.; Shi, Z. G. Talanta 2018, 178, 583.
[36] Kucerova, G.; Kalikova, K.; Tesarova, E. Chirality 2017, 29, 239.
[37] Roy, D.; Armstrong, D. W. J. Chromatogr. A 2019, 1605.
[38] Patel, D. C.; Breitbach, Z. S.; Wahab, M. F.; Barhate, C. L.; Armstrong, D. W. Anal. Chem. 2015, 87, 9137.
[39] Wahab, M. F.; Wimalasinghe, R. M.; Wang, Y.; Barhate, C. L.; Patel, D. C.; Armstrong, D. W. Anal. Chem. 2016, 88, 8821.
[40] Guo, H.; Wahab, M. F.; Berthod, A.; Armstrong, D. W. J. Pharm. Anal. 2018, 8, 324.
[41] Franzini, R.; Ciogli, A.; Gasparrini, F.; Ismail, O. H.; Villani, C. In Chiral Analysis, Elsevier Science, Rome, Italy, 2018, pp. 607~629.
[42] West, C. TrAC, Trends Anal. Chem. 2019, 120.
[43] Speybrouck, D.; Lipka, E. J. Chromatogr. A 2016, 1467, 33.
[44] Biba, M.; Regalado, E. L.; Wu, N.; Welch, C. J. J. Chromatogr. A 2014, 1363, 250.
[45] Patel, D. C.; Breitbach, Z. S.; Yu, J.; Nguyen, K. A.; Armstrong, D. W. Anal. Chim. Acta 2017, 963, 164.
[46] Berger, T. A. J. Chromatogr. A 2016, 1459, 136.
[47] Li, D. Y.; Wu, X.; Hao, F. L.; Yang, Y.; Chen, X. M. Chin. J. Chromatogr. 2016, 34, 80(in Chinese). (李冬艳, 吴锡, 郝芳丽, 杨洋, 陈小明, 色谱, 2016, 34, 80.)
[48] Heiland, J. J.; Geissler, D.; Piendl, S. K.; Warias, R.; Belder, D. Anal. Chem. 2019, 91, 6134.
[49] Zhang, W. H.; Xie, W.; Hou, J. B.; Chen, Q. K.; Li, S. M.; Zhu, Z. L.; Zou, X. Q; Xu, D. M. Chin. J. Chromatogr. 2019 37, 1356(in Chinese). (张文华, 谢文, 侯建波, 陈钦可, 李淑敏, 祝泽龙, 邹学权, 徐敦明, 色谱, 2019, 37, 1356.)
[50] Yang, F.; Tang, G.; Liu, S.; Fan, Z.; Wang, Y.; Deng, H.; Bian, Z.; Li, Z. Chirality 2019, 31, 353.
[51] Tao, Y.; Zheng, Z.; Yu, Y.; Xu, J.; Liu, X.; Wu, X.; Dong, F.; Zheng, Y. Food Chem. 2018, 241, 32.
[52] Zhang, X.; Zhao, Y.; Cui, X.; Wang, X.; Shen, H.; Chen, Z.; Huang, C.; Meruva, N.; Zhou, L.; Wang, F.; Wu, L.; Luo, F. J. Chromatogr. A 2018, 1581-1582, 144.
[53] León-González, M. E.; Rosales-Conrado, N.; Pérez-Arribas, L. V.; Guillén-Casla, V. Biomed. Chromatogr. 2014, 28, 59.
[54] D'Atri, V.; Fekete, S.; Clarke, A.; Veuthey, J. L.; Guillarme, D. Anal. Chem. 2019, 91, 210.
[55] Barhate, C. L.; Joyce, L. A.; Makarov, A. A.; Zawatzky, K.; Bernardoni, F.; Schafer, W. A.; Armstrong, D. W.; Welch, C. J.; Regalado, E. L. Chem. Commun. 2017, 53, 509.
[56] Barhate, C. L.; Regalado, E. L.; Contrella, N. D.; Lee, J.; Jo, J.; Makarov, A. A.; Armstrong, D. W.; Welch, C. J. Anal. Chem. 2017, 89, 3545.
[57] Ianni, F.; Sardella, R.; Lisanti, A.; Gioiello, A.; Cenci Goga, B. T.; Lindner, W.; Natalini, B. J. Pharm. Biomed. Anal. 2015, 116, 40.
[58] Rao, R. N.; Kumar, K. N.; Shinde, D. D. J. Pharm. Biomed. Anal. 2010, 52, 398.
[59] Venkatramani, C. J.; Al-Sayah, M.; Li, G.; Goel, M.; Girotti, J.; Zang, L.; Wigman, L.; Yehl, P.; Chetwyn, N. Talanta 2016, 148, 548.
[60] Woiwode, U.; Neubauer, S.; Lindner, W.; Buckenmaier, S.; Lämmerhofer, M. J. Chromatogr. A 2018, 1562, 69.
[61] Woiwode, U.; Reischl, R. J.; Buckenmaier, S.; Lindner, W.; Lämmerhofer, M. Anal. Chem. 2018, 90, 7963.
[62] Iguiniz, M.; Corbel, E.; Roques, N.; Heinisch, S. J. Pharm. Biomed. Anal. 2018, 159, 237.
[63] Venkatramani, C. J.; Al-Sayah, M.; Li, G.; Goel, M.; Girotti, J.; Zang, L.; Wigman, L.; Yehl, P.; Chetwyn, N. Talanta 2016, 148, 548.
[64] Barhate, C. L.; Regalado, E. L.; Contrella, N. D.; Lee, J.; Jo, J.; Makarov, A. A.; Armstrong, D. W.; Welch, C. J. Anal. Chem. 2017, 89, 3545.
[65] Bester, K.; Vorkamp, K. Anal Bioanal Chem 2013, 405, 6519.
[66] Woiwode, U.; Reischl, R. J.; Buckenmaier, S.; Lindner, W.; Lammerhofer, M. Anal. Chem. 2018, 90, 7963.
[67] Schiller, D. S.; Fung, H. B. Clin. Ther. 2007, 29, 1862.
[68] Xu, F.; Xu, Y.; Liu, G.; Zhang, M.; Qiang, S.; Kang, J. J Chromatogr. A 2020, 460845.

超快速和二维液相色谱手性分离

Chiral Separation by Ultrafast and Two-Dimensional Liquid Chromatography

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