Citation: Hui Li, Xiaoping Wang, Chengxiang Shi, Liang Zhao, Zuguang Li, Hongdeng Qiu. Chiral phenethylamine synergistic tricarboxylic acid modified β-cyclodextrin immobilized on porous silica for enantioseparation[J]. Chinese Chemical Letters, ;2023, 34(3): 107606. doi: 10.1016/j.cclet.2022.06.029 shu

Chiral phenethylamine synergistic tricarboxylic acid modified β-cyclodextrin immobilized on porous silica for enantioseparation

Hui Li ^{a, 1} ,
Xiaoping Wang ^{b, 1} ,
Chengxiang Shi ^a ,
Liang Zhao ^a ,
Zuguang Li ^{b, *,} ,
Hongdeng Qiu ^{a, *,}

a.
CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
b.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China

lzg@zjut.edu.cn

hdqiu@licp.cas.cn

Received Date: 10 February 2022
Revised Date: 1 June 2022
Accepted Date: 13 June 2022
Available Online: 16 June 2022

Figures(4)

In this work, a series of chiral phenethylamine synergistic tricarboxylic acid modified β-cyclodextrin bonded stationary phase for high performance liquid chromatography (HPLC) were synthesized via a simple one-pot synthesis approach. Various racemates (aryl alcohols, flavanones, triazoles, benzoin, etc.) were well separated on the tricarboxylic acid modified chiral stationary phases in both normal and reversed modes with good reproducibility and stability, and the influence of mobile phase composition on resolution (R_s) were deeply investigated. The RSD values of R_s for repeatability and column-to-column were below 1.28% and 3.05%, respectively. Hence, the fabrication of tricarboxylic acid modified chiral stationary phase (CSPs) is a new efficient strategy to improve the application of β-cyclodextrin as CSPs in the field of chromatography.
- Tricarboxylic acid,
- β-cyclodextrin,
- Chiral stationary phases,
- Enantioseparation,
- One-pot strategy
1. [1]
  Y. Shuang, T. Zhang, L. Li, J. Chromatogr. A 1614 (2020) 460702. doi: 10.1016/j.chroma.2019.460702
2. [2]
  J. Znaleziona, I. Fejos, J. Ševcík, et al., J. Pharm. Biomed. Anal. 105 (2015) 10–16. doi: 10.1016/j.jpba.2014.11.027
3. [3]
  X. Wang, H. Li, K. Quan, et al., J. Chromatogr. A 1651 (2021) 462338. doi: 10.1016/j.chroma.2021.462338
4. [4]
  X. Lu, M. Chen, J. Yang, et al., J. Chromatogr. A 1664 (2022) 462786. doi: 10.1016/j.chroma.2021.462786
5. [5]
  L. Li, X. Xue, H. Zhang, et al., Chin. Chem. Lett. 32 (2021) 2139–2142. doi: 10.1016/j.cclet.2020.11.022
6. [6]
  Z. Liu, K. Quan, H. Li, et al., J. Anal. Test. 5 (2021) 242–257. doi: 10.1007/s41664-021-00155-2
7. [7]
  P. Zuvela, M. Skoczylas, J.J. Liu, et al., Chem. Rev. 119 (2019) 3674–3729. doi: 10.1021/acs.chemrev.8b00246
8. [8]
  Y. Zhang, X. Jin, X. Ma, et al., Anal. Methods 13 (2021) 8–33. doi: 10.1039/D0AY01831G
9. [9]
  J. Gao, G. Luo, Z. Li, et al., J. Chromatogr. A 1618 (2020) 460885. doi: 10.1016/j.chroma.2020.460885
10. [10]
  J. Sun, S. Ma, B. Liu, et al., Talanta 204 (2019) 817–825. doi: 10.1016/j.talanta.2019.06.071
11. [11]
  Y. Yan, Y. Zhang, Y. Chen, et al., ACS Appl. Polym. Mater. 2 (2020) 5641–5645. doi: 10.1021/acsapm.0c00958
12. [12]
  X. Wang, H. Li, K. Quan, et al., Talanta 225 (2021) 121987. doi: 10.1016/j.talanta.2020.121987
13. [13]
  H. Li, K. Quan, X. Yang, et al., TrAC Trends Anal. Chem. 131 (2020) 116026. doi: 10.1016/j.trac.2020.116026
14. [14]
  C. Shi, H. Li, X. Shi, et al., Chin. Chem. Lett. 33 (2022) 3613–3622. doi: 10.1016/j.cclet.2021.12.010
15. [15]
  X.L. Lu, M. Chen, J.T. Yang, et al., J. Chromatogr. A 1664 (2022) 462786. doi: 10.1016/j.chroma.2021.462786
16. [16]
  X.B. Yao, H. Zheng, Y. Zhang, et al., Anal. Chem. 88 (2016) 4955–4964. doi: 10.1021/acs.analchem.6b00897
17. [17]
  L. Wang, S. Dong, F. Han, et al., J. Chromatogr. A 1383 (2015) 70–78. doi: 10.1016/j.chroma.2015.01.023
18. [18]
  M. Meng, M. Ma, J. Yi, et al., Sep. Sci. Plus 2 (2019) 4–11. doi: 10.1002/sscp.201800132
19. [19]
  C.M. Wu, T.Y. Li, D.J. Li, et al., Chin. Chem. Lett. 32 (2021) 2174–2178. doi: 10.1016/j.cclet.2020.11.060
20. [20]
  K. Lin, W.P. Liu, L. Li, et al., J. Agric. Food Chem. 56 (2008) 4273–4277. doi: 10.1021/jf073535l
21. [21]
  M. Fu, Y. Xu, Y. Chen, et al., Food Chem. 230 (2017) 649–656. doi: 10.1016/j.foodchem.2017.03.098
22. [22]
  W. Shimizu, N. Uemura, Y. Yoshida, et al., Cryst. Growth Des. 20 (2020) 5676–5681. doi: 10.1021/acs.cgd.0c00955
23. [23]
  B.A. Graf, P.E. Milbury, J.B. Blumberg, J. Med. Food 8 (2005) 281–290. doi: 10.1089/jmf.2005.8.281
24. [24]
  S. Akbar, F. Subhan, M. Shahid, et al., Eur. J. Pharmacol. 872 (2020) 172972. doi: 10.1016/j.ejphar.2020.172972
25. [25]
  N.M. Hegazi, A.N. Hashim, Pharmazie 71 (2016) 544–547.
26. [26]
  P. Srivarangkul, W. Yuttithamnon, A. Suroengrit, et al., Antivir. Res. 151 (2018) 27–38. doi: 10.1016/j.antiviral.2018.01.010
27. [27]
  D.D. Cao, T.Q. Do, H.D.T. Mai, et al., Nat. Prod. Lett. 34 (2020) 413–420. doi: 10.1080/14786419.2018.1538219
28. [28]
  T. Ishikawa, Heterocycles 53 (2000) 453–474. doi: 10.3987/REV-99-526
29. [29]
  H.I.C. Lowe, N.J. Toyang, C.T. Watson, et al., Cancer Cell Int. 17 (2017) 38–49. doi: 10.1186/s12935-017-0404-z
30. [30]
  J. Zhang, S. Zhuang, C. Tong, et al., J. Agric. Food Chem. 61 (2013) 7203–7211. doi: 10.1021/jf401095n
31. [31]
  D.J. Sheehan, C.A. Hitchcock, C.M. Sibley, Clin. Microbiol. Rev. 12 (1999) 40–79. doi: 10.1128/CMR.12.1.40
32. [32]
  A.K. Goetz, H.Z. Ren, J.E. Schmid, et al., Toxicol. Sci. 95 (2007) 227–239. doi: 10.1093/toxsci/kfl124
33. [33]
  J.J. Manclús, M.J. Moreno, E. Plana, et al., Food Chem. 56 (2008) 8793–8800. doi: 10.1021/jf801187b
34. [34]
  J. Li, C. Dong, W. An, et al., J. Agric. Food Chem. 68 (2020) 5969–5979. doi: 10.1021/acs.jafc.0c01385
35. [35]
  Y. Li, F. Dong, X. Liu, et al., Environ. Sci. Technol. 46 (2012) 2675–2683. doi: 10.1021/es203320x
36. [36]
  F. Dong, J. Li, B. Chankvetadze, et al., Environ. Sci. Technol. 47 (2013) 3386–3394. doi: 10.1021/es304982m
37. [37]
  R. He, B. Mai, J. Fan, et al., J. Agric. Food Chem. 67 (2019) 10782–10790. doi: 10.1021/acs.jafc.9b03632
38. [38]
  X.L. Pan, Y.P. Cheng, F.S. Dong, et al., J. Hazard. Mater. 359 (2018) 194–202. doi: 10.1016/j.jhazmat.2018.07.061
39. [39]
  Q. Zhang, Z.X. Zhang, B.W. Tang, et al., J. Agric. Food Chem. 66 (2018) 7286–7293. doi: 10.1021/acs.jafc.8b01771
40. [40]
  B. Tang, W. Wang, H. Hou, et al., Chin. Chem. Lett. 33 (2022) 898–902. doi: 10.1016/j.cclet.2021.06.089
41. [41]
  J. Chen, N. Yuan, D. Jiang, et al., Chin. Chem. Lett. 32 (2021) 3398–3401. doi: 10.1016/j.cclet.2021.04.052
42. [42]
  J. Gao, L.X. Chen, Q. Wu, et al., Chirality 31 (2019) 669–681. doi: 10.1002/chir.23082
43. [43]
  Y. Shuang, Y. Liao, H. Wang, et al., Chirality 32 (2020) 168–184. doi: 10.1002/chir.23147
44. [44]
  X.X. Li, X. Jin, X.B. Yao, et al., J. Chromatogr. A 1467 (2016) 279–287. doi: 10.1016/j.chroma.2016.06.074
45. [45]
  J.J. Zhang, S.Y. Wang, P. Zhang, et al., Chin. Chem. Lett. 33 (2022) 3873–3878. doi: 10.1016/j.cclet.2021.11.081
46. [46]
  Y.F. Wu, Y. Xiao, X.P. Wang, et al., ACS Sens. 4 (2019) 2009–2017. doi: 10.1021/acssensors.9b00270
47. [47]
  J. Zhou, B. Yang, J. Tang, et al., J. Chromatogr. A 1467 (2016) 169–177. doi: 10.1016/j.chroma.2016.06.030
48. [48]
  Y. Lin, J. Zhou, J. Tang, et al., J. Chromatogr. A 1406 (2015) 342–346. doi: 10.1016/j.chroma.2015.06.051
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