Citation: Zhou Min, Long Yuande, Zhi Yonggang, Xu Xiaoying. Preparation and chromatographic evaluation of a chiral stationary phase based on carboxymethyl-β-cyclodextrin for high-performance liquid chromatography[J]. Chinese Chemical Letters, ;2018, 29(9): 1399-1403. doi: 10.1016/j.cclet.2017.10.039 shu

Preparation and chromatographic evaluation of a chiral stationary phase based on carboxymethyl-β-cyclodextrin for high-performance liquid chromatography

Zhou Min ^a,b ,
Long Yuande ^a,, ,
Zhi Yonggang ^a ,
Xu Xiaoying ^a

a.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 640041, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Long Yuande, ydlong@cioc.ac.cn
Received Date: 15 August 2017
Revised Date: 27 October 2017
Accepted Date: 30 October 2017
Available Online: 10 September 2017

Figures(2)

A chiral stationary phase (CSP) was prepared by chemically bonding carboxymethyl-β-cyclodextrin (CM-β-CD) onto 3-aminopropyl silica gel through amidation reaction in water solution and was characterized by Fourier transform infrared spectroscopy (FT-IR), element analysis (EA) and thermal gravimetry analysis (TGA). The chromatographic performance was evaluated with 24 racemates under reversedphase conditions. The effect of salt, organic modifier, mobile phase pH and structures of analytes were discussed. In comparison with native β-CD bonded column, CYCLOBOND I 2000, CM-β-CD CSP exhibited enhanced enantioseparation.
- Enantioseparation,
- Carboxymethyl-β-cyclodextrin,
- Chiral stationary phase,
- Chemical bonding,
- Reversed-phase
1. [1]
  J. Caldwell, J. Chromatogr. A 719(1996) 3-13. doi: 10.1016/0021-9673(95)00465-3
2. [2]
  M. Huang, X.F. Zhang, Y. Wang, et al., Chin. Chem. Lett. 24(2013) 840-844. doi: 10.1016/j.cclet.2013.05.019
3. [3]
  J.C. Ye, W.Y. Yu, S. Zeng, et al., Biomed. Chromatogr. 24(2010) 799-807. doi: 10.1002/bmc.v24:8
4. [4]
  J. Guan, J. Yang, F.M. Li, et al., J. Sep. Sci. 31(2008) 288-293. doi: 10.1002/(ISSN)1615-9314
5. [5]
  S.L. Ma, S. Shen, N. Grinberg, et al., J. Chromatogr. A 1216(2009) 1232-1240. doi: 10.1016/j.chroma.2008.12.016
6. [6]
  Y.P. Zhang, X.M. Liang, A.W. Lei, et al., J. Chromatogr. A 1191(2008) 188-192. doi: 10.1016/j.chroma.2007.11.018
7. [7]
  X.P. Chen, H. Yuan, Z.M. Zhou, et al., Chin. Chem. Lett. 19(2008) 797-800. doi: 10.1016/j.cclet.2008.04.045
8. [8]
  Q.J. Peng, J.J. Yang, Chin. Chem. Lett. 25(2014) 1416-1418. doi: 10.1016/j.cclet.2014.05.052
9. [9]
  T.G. Lu, M.J. Yang, Chin. J. Chromatogr. 25(2007) 830-833.
10. [10]
  S.M. Shuang, M.M.F. Choi, J. Chromatogr. A 919(2001) 321-329. doi: 10.1016/S0021-9673(01)00810-X
11. [11]
  M.H. Zhai, L.Q. Su, Y.J. Sun, Chem. Res. Appl. 24(2012) 450-453.
12. [12]
  Y.J. Shi, C.H. Huo, B.J. Xu, et al., J. Chromatogr. A 1072(2005) 279-282. doi: 10.1016/j.chroma.2005.03.027
13. [13]
  C. Roussel, A. Favrou, J. Chromatogr. A 704(1995) 67-74. doi: 10.1016/0021-9673(95)00166-K
14. [14]
  S.Y. Park, J.K. Park, J.H. Park, et al., Microchem. J. 70(2001) 179-185. doi: 10.1016/S0026-265X(01)00129-1
15. [15]
  F. Leonelli, B. Garofalo, M. Sinibaldi, et al., J. Liq. Chromatogr. Related Technol. 26(2003) 409-424. doi: 10.1081/JLC-120017179
16. [16]
  A. Berthod, C.D. Chang, D.W. Amstrong, Talanta 40(1993) 1367-1373. doi: 10.1016/0039-9140(93)80212-A
17. [17]
  L. Chen, L.F. Zhang, S.C. Ng, et al., J. Chromatogr. A 950(2002) 65-74. doi: 10.1016/S0021-9673(02)00043-2
18. [18]
  Y. Machida, H. Nishi, K. Nakamura, J. Chromatogr. A 830(1999) 311-320. doi: 10.1016/S0021-9673(98)00896-6
19. [19]
  H. Hashem, T. Jira, J. Chromatogr. A 1133(2006) 69-75. doi: 10.1016/j.chroma.2006.07.074
20. [20]
  H. Hashem, C. Trundelberg, T. Jira, et al., J. Chromatogr. A 1218(2011) 6727-6731. doi: 10.1016/j.chroma.2011.07.090
21. [21]
  P. Nikitas, A. Pappa-Louisi, J. Chromatogr. A 971(2002) 47-60. doi: 10.1016/S0021-9673(02)00965-2
22. [22]
  R. LoBrutto, A. Jones, Y.V. Kazakevich, et al., J. Chromatogr. A 913(2001) 173-187. doi: 10.1016/S0021-9673(00)01012-8
23. [23]
  R. Sardella, F. Ianni, B. Natalini, et al., Biomed. Chromatogr. 28(2014) 159-167. doi: 10.1002/bmc.3015
24. [24]
  Y. Wang, T.T. Ong, S.C. Ng, et al., J. Chromatogr. A 1216(2009) 2388-2393. doi: 10.1016/j.chroma.2009.01.039
25. [25]
  K. Fujimura, S. Suzuki, K. Hayashi, et al., Anal. Chem. 62(1990) 2198-2205. doi: 10.1021/ac00219a009
26. [26]
  A. Berthod, J.D. Duncan, D.W. Armstrong, et al., J. Pharm. Biomed. Anal. 8(1990) 123-130. doi: 10.1016/0731-7085(90)80018-K
27. [27]
  M. Rekharsky, Y. Inoue, J. Am. Chem. Soc. 122(2000) 4418-4435. doi: 10.1021/ja9921118
28. [28]
  Q.F. Huang, Y. Inoue, C. Yang, et al., J. Org. Chem. 81(2016) 3430-3434. doi: 10.1021/acs.joc.6b00130
29. [29]
  Z.Q. Yan, Q.F. Huang, C. Yang, et al., Org. Lett. 19(2017) 898-901. doi: 10.1021/acs.orglett.7b00057
30. [30]
  D. Zhao, Y. Chen, Y. Liu, Chin. Chem. Lett. 26(2015) 829-833. doi: 10.1016/j.cclet.2014.11.028
31. [31]
  J.C. Gui, Z.Q. Yan, C. Yang, et al., Chin. Chem. Lett. 27(2016) 1017-1021. doi: 10.1016/j.cclet.2016.04.021
32. [32]
  A.M. Stalcup, S.C. Chang, D.W. Armstrong, J. Chromatogr. 513(1990) 181-194. doi: 10.1016/S0021-9673(01)89435-8
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