Citation: Xu Yao, Kang Jingwu. Chiral Separation by Ultrafast and Two-Dimensional Liquid Chromatography[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3794-3801. doi: 10.6023/cjoc202005046 shu

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

Corresponding author: Kang Jingwu, jingwu.kang@sioc.ac.cn
Received Date: 18 May 2020
Revised Date: 29 June 2020
Available Online: 15 July 2020
Fund Project: the National Natural Science Foundation of China 21375140the National Natural Science Foundation of China 21175146the National Natural Science Foundation of China 21775158Project supported by the National Natural Science Foundation of China (Nos. 21775158, 21375140, 21175146)

Figures(6)

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.
- ultrafast liquid chromatography,
- two-dimensional liquid chromatography,
- chiral separation,
- high-throughput separation
1. [1]
  De Camp, W. H. J. Pharm. Biomed. Anal. 1993, 11, 1167. doi: 10.1016/0731-7085(93)80100-F
2. [2]
  Maier, N. M.; Franco, P.; Lindner, W. J. Chromatogr. A 2001, 906, 3. doi: 10.1016/S0021-9673(00)00532-X
3. [3]
  Hegade, R. S.; Lynen, F. J. Chromatogr. A 2019, 1586, 116. doi: 10.1016/j.chroma.2018.12.008
4. [4]
  Pirok, B. W. J.; Stoll, D. R.; Schoenmakers, P. J. Anal. Chem. 2019, 91, 240. doi: 10.1021/acs.analchem.8b04841
5. [5]
  Lorenz, H.; Seidel-Morgenstern, A. Angew. Chem., Int. Ed. 2014, 53, 1218. doi: 10.1002/anie.201302823
6. [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. doi: 10.1039/c3ob42195c
7. [7]
  Major, E. R. LC GC Europe 2012, 25, 1.
8. [8]
  Mazzeo, J. R.; Neue, U. D.; Kele, M.; Plumb, R. S. Anal. Chem. 2005, 77, 460 A.
9. [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. doi: 10.1016/j.chroma.2017.05.039
10. [10]
  MacNair, J. E.; Lewis, K. C.; Jorgenson, J. W. Anal. Chem. 1997, 69, 983. doi: 10.1021/ac961094r
11. [11]
  Jorgenson, J. W. Annu. Rev. Anal. Chem. 2010, 3, 129. doi: 10.1146/annurev.anchem.1.031207.113014
12. [12]
  Perera, D.; Tucker, J. W.; Brahmbhatt, S.; Helal, C. J.; Chong, A.; Farrell, W.; Richardson, P.; Sach, N. W. Science 2018, 359, 429. doi: 10.1126/science.aap9112
13. [13]
  Robbins, D. W.; Hartwig, J. F. Science 2011, 333, 1423. doi: 10.1126/science.1207922
14. [14]
  Barhate, C. L.; Wahab, M. F.; Tognarelli, D. J.; Berger, T. A.; Armstrong, D. W. Anal. Chem. 2016, 88, 8664. doi: 10.1021/acs.analchem.6b01898
15. [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. doi: 10.1016/j.chroma.2015.11.071
16. [16]
  Patel, D. C.; Breitbach, Z. S.; Wahab, M. F.; Barhate, C. L.; Armstrong, D. W. Anal. Chem. 2015, 87, 9137. doi: 10.1021/acs.analchem.5b00715
17. [17]
  Regalado, E. L.; Welch, C. J. J. Sep. Sci. 2015, 38, 2826. doi: 10.1002/jssc.201500270
18. [18]
  Wahab, M. F.; Wimalasinghe, R. M.; Wang, Y.; Barhate, C. L.; Patel, D. C.; Armstrong, D. W. Anal. Chem. 2016, 88, 8821. doi: 10.1021/acs.analchem.6b02260
19. [19]
  Welch, C. J.; Regalado, E. L. J. Sep. Sci. 2014, 37, 2552. doi: 10.1002/jssc.201400508
20. [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. doi: 10.1021/ac301335b
21. [21]
  Barhate, C. L.; Wahab, M. F.; Breitbach, Z. S.; Bell, D. S.; Armstrong, D. W. Anal. Chim. Acta 2015, 898, 128. doi: 10.1016/j.aca.2015.09.048
22. [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. doi: 10.1016/j.chroma.2015.11.071
23. [23]
  Kirkland, J. J.; Langlois, T. J.; DeStefano, J. J. Am. Lab. 2007, 39, 18.
24. [24]
  Gritti, F.; Leonardis, I.; Abia, J.; Guiochon, G. J. Chromatogr. A 2010, 1217, 3819. doi: 10.1016/j.chroma.2010.04.026
25. [25]
  Guiochon, G.; Gritti, F. J. Chromatogr. A 2011, 1218, 1915. doi: 10.1016/j.chroma.2011.01.080
26. [26]
  Hayes, R.; Ahmed, A.; Edge, T.; Zhang, H. J. Chromatogr. A 2014, 1357, 36. doi: 10.1016/j.chroma.2014.05.010
27. [27]
  Jandera, P.; Hájek, T.; Staňková, M. Anal. Bioanal. Chem. 2015, 407, 139. doi: 10.1007/s00216-014-8147-3
28. [28]
  Tanaka, N.; McCalley, D. V. Anal. Chem. 2016, 88, 279. doi: 10.1021/acs.analchem.5b04093
29. [29]
  Reischl, R. J.; Hartmanova, L.; Carrozzo, M.; Huszar, M.; Fruhauf, P.; Lindner, W. J. Chromatogr. A 2011, 1218, 8379. doi: 10.1016/j.chroma.2011.09.046
30. [30]
  Lomsadze, K.; Jibuti, G.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2012, 1234, 50. doi: 10.1016/j.chroma.2012.01.084
31. [31]
  Kharaishvili, Q.; Jibuti, G.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2016, 1467, 163. doi: 10.1016/j.chroma.2016.08.046
32. [32]
  Berger, T. A. J. Chromatogr. A 2017, 1510, 82. doi: 10.1016/j.chroma.2017.06.021
33. [33]
  Bezhitashvili, L.; Bardavelidze, A.; Mskhiladze, A.; Gumustas, M.; Ozkan, S. A.; Volonterio, A.; Farkas, T.; Chankvetadze, B. J. Chromatogr. A 2018, 1571, 132. doi: 10.1016/j.chroma.2018.08.011
34. [34]
  D'Orazio, G.; Kakava, R.; Volonterio, A.; Fanali, S.; Chankvetadze, B. Electrophoresis 2017, 38, 1932. doi: 10.1002/elps.201700126
35. [35]
  Mao, X. J.; Li, J.; Liu, D.; Qiao, T.; Ma, L.; Sun, X.; Xu, L.; Shi, Z. G. Talanta 2018, 178, 583. doi: 10.1016/j.talanta.2017.09.093
36. [36]
  Kucerova, G.; Kalikova, K.; Tesarova, E. Chirality 2017, 29, 239. doi: 10.1002/chir.22701
37. [37]
  Roy, D.; Armstrong, D. W. J. Chromatogr. A 2019, 1605.
38. [38]
  Patel, D. C.; Breitbach, Z. S.; Wahab, M. F.; Barhate, C. L.; Armstrong, D. W. Anal. Chem. 2015, 87, 9137. doi: 10.1021/acs.analchem.5b00715
39. [39]
  Wahab, M. F.; Wimalasinghe, R. M.; Wang, Y.; Barhate, C. L.; Patel, D. C.; Armstrong, D. W. Anal. Chem. 2016, 88, 8821. doi: 10.1021/acs.analchem.6b02260
40. [40]
  Guo, H.; Wahab, M. F.; Berthod, A.; Armstrong, D. W. J. Pharm. Anal. 2018, 8, 324. doi: 10.1016/j.jpha.2018.08.001
41. [41]
  Franzini, R.; Ciogli, A.; Gasparrini, F.; Ismail, O. H.; Villani, C. In Chiral Analysis, Elsevier Science, Rome, Italy, 2018, pp. 607~629.
42. [42]
  West, C. TrAC, Trends Anal. Chem. 2019, 120.
43. [43]
  Speybrouck, D.; Lipka, E. J. Chromatogr. A 2016, 1467, 33. doi: 10.1016/j.chroma.2016.07.050
44. [44]
  Biba, M.; Regalado, E. L.; Wu, N.; Welch, C. J. J. Chromatogr. A 2014, 1363, 250. doi: 10.1016/j.chroma.2014.07.010
45. [45]
  Patel, D. C.; Breitbach, Z. S.; Yu, J.; Nguyen, K. A.; Armstrong, D. W. Anal. Chim. Acta 2017, 963, 164. doi: 10.1016/j.aca.2017.02.005
46. [46]
  Berger, T. A. J. Chromatogr. A 2016, 1459, 136. doi: 10.1016/j.chroma.2016.07.012
47. [47]
  Li, D. Y.; Wu, X.; Hao, F. L.; Yang, Y.; Chen, X. M. Chin. J. Chromatogr. 2016, 34, 80(in Chinese).
48. [48]
  Heiland, J. J.; Geissler, D.; Piendl, S. K.; Warias, R.; Belder, D. Anal. Chem. 2019, 91, 6134. doi: 10.1021/acs.analchem.9b00726
49. [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).
50. [50]
  Yang, F.; Tang, G.; Liu, S.; Fan, Z.; Wang, Y.; Deng, H.; Bian, Z.; Li, Z. Chirality 2019, 31, 353. doi: 10.1002/chir.23062
51. [51]
  Tao, Y.; Zheng, Z.; Yu, Y.; Xu, J.; Liu, X.; Wu, X.; Dong, F.; Zheng, Y. Food Chem. 2018, 241, 32. doi: 10.1016/j.foodchem.2017.08.038
52. [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. doi: 10.1016/j.chroma.2018.10.051
53. [53]
  León-González, M. E.; Rosales-Conrado, N.; Pérez-Arribas, L. V.; Guillén-Casla, V. Biomed. Chromatogr. 2014, 28, 59. doi: 10.1002/bmc.3007
54. [54]
  D'Atri, V.; Fekete, S.; Clarke, A.; Veuthey, J. L.; Guillarme, D. Anal. Chem. 2019, 91, 210. doi: 10.1021/acs.analchem.8b05026
55. [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. doi: 10.1039/C6CC08512A
56. [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. doi: 10.1021/acs.analchem.6b04834
57. [57]
  Ianni, F.; Sardella, R.; Lisanti, A.; Gioiello, A.; Cenci Goga, B. T.; Lindner, W.; Natalini, B. J. Pharm. Biomed. Anal. 2015, 116, 40. doi: 10.1016/j.jpba.2014.12.041
58. [58]
  Rao, R. N.; Kumar, K. N.; Shinde, D. D. J. Pharm. Biomed. Anal. 2010, 52, 398. doi: 10.1016/j.jpba.2009.09.020
59. [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. doi: 10.1016/j.talanta.2015.10.054
60. [60]
  Woiwode, U.; Neubauer, S.; Lindner, W.; Buckenmaier, S.; Lämmerhofer, M. J. Chromatogr. A 2018, 1562, 69. doi: 10.1016/j.chroma.2018.05.062
61. [61]
  Woiwode, U.; Reischl, R. J.; Buckenmaier, S.; Lindner, W.; Lämmerhofer, M. Anal. Chem. 2018, 90, 7963. doi: 10.1021/acs.analchem.8b00676
62. [62]
  Iguiniz, M.; Corbel, E.; Roques, N.; Heinisch, S. J. Pharm. Biomed. Anal. 2018, 159, 237. doi: 10.1016/j.jpba.2018.06.058
63. [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. doi: 10.1016/j.talanta.2015.10.054
64. [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. doi: 10.1021/acs.analchem.6b04834
65. [65]
  Bester, K.; Vorkamp, K. Anal Bioanal Chem 2013, 405, 6519. doi: 10.1007/s00216-013-7100-1
66. [66]
  Woiwode, U.; Reischl, R. J.; Buckenmaier, S.; Lindner, W.; Lammerhofer, M. Anal. Chem. 2018, 90, 7963. doi: 10.1021/acs.analchem.8b00676
67. [67]
  Schiller, D. S.; Fung, H. B. Clin. Ther. 2007, 29, 1862. doi: 10.1016/j.clinthera.2007.09.015
68. [68]
  Xu, F.; Xu, Y.; Liu, G.; Zhang, M.; Qiang, S.; Kang, J. J Chromatogr. A 2020, 460845.
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