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Vol. 25 No. 2 (2013): Vol 25 Issue 2

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Comparative Enantioseparation of Crufomate with Cellulose- and Amylose-based Chiral Stationary Phases on Reverse-Phase and Normal-Phase High-Performance Liquid Chromatography

https://doi.org/10.14233/ajchem.2013.12908
Tingting Chai
Key Laboratory of Food and Biotechnology, Department of Bioengineering, School of Biotechnology and Food Science, Tianjin University of Commerce, Tianjin 300134, P.R. China ; Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China
Xueqing Wang
Key Laboratory of Food and Biotechnology, Department of Bioengineering, School of Biotechnology and Food Science, Tianjin University of Commerce, Tianjin 300134, P.R. China
Mei Bie
Key Laboratory of Food and Biotechnology, Department of Bioengineering, School of Biotechnology and Food Science, Tianjin University of Commerce, Tianjin 300134, P.R. China ; Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China
Shouhui Dai
Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China
Hualin Zhao
Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China
Shuming Yang
Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China
Jing Qiu
Institute of Quality Standards and Testing Technology for Agro-Products, Key Laboratory of Agro-product Quality and Safety, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R. China

Corresponding Author(s) : Jing Qiu

jinn.qiu@hotmail.com

Asian Journal of Chemistry, Vol. 25 No. 2 (2013): Vol 25 Issue 2

Abstract

This study used cellulose- and amylose-based chiral stationary phases to comparatively separate crufomate enantiomers on reverse-phase and normal-phase high performance liquid chromatography (RP-HPLC and NP-HPLC). The baseline separations were obtained on Phenomene Lux cellulose-1, Lux cellulose-2 and Lux amylose-2 with 2-propanol/hexane and on Lux cellulose-1 and Lux amylose-2 with acetonitrile/water as mobile phase. The results of optical rotation detections showed that (+)-enantiomer of crufomate was firstly eluted on Lux cellulose-1 and Lux amylose-2 both on NP-HPLC and RP-HPLC, while the (-)-enantiomer was firstly eluted on Lux cellulose-2 and Lux cellulose-3 on NP-HPLC. The influences of column temperature from 5-40 ºC on separation were investigated on three chiral stationary phases. The thermodynamic parameters were calculated using van't Hoff equations to study the enthalpy-driven and entropy-driven process. This work will be helpful to prepare optical pure enantiomers and establish efficient analytical method for study on enantioselective behaviours of crufomate.

Keywords

Crufomate Enantiomeric separation HPLC Elution order Optical rotation
Chai, T., Wang, X., Bie, M., Dai, S., Zhao, H., Yang, S., & Qiu, J. (2012). Comparative Enantioseparation of Crufomate with Cellulose- and Amylose-based Chiral Stationary Phases on Reverse-Phase and Normal-Phase High-Performance Liquid Chromatography. Asian Journal of Chemistry, 25(2), 797–802. https://doi.org/10.14233/ajchem.2013.12908
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References
  1. L.G. Costa, Clin. Chim. Acta, 366, 1 (2006).
  2. B.K. Singh and A. Walker, FEMS Microbiol. Rev., 30, 428 (2006).
  3. N. Kurihara and J. Miyamoto, Chirality in Agrochemicals, John Wiley & Sons, Chichester (1998).
  4. A.S. Garay, Nature, 271, 186 (1987).
  5. A.W. Garrison, Green Chem., 6, 77 (2004).
  6. J. Jarman, W. Jones, L. Howell and A.W. Garrison, J. Agric. Food Chem., 53, 6175 (2005).
  7. J.J. Ellington, J.J. Evans and K. Prickett, J. Chromatogr. A, 928, 145 (2001).
  8. Y. Wang, K. Tai and J. Yen, Ecotoxicol. Environ. Safety, 57, 346 (2004).
  9. M.G. Nillos, J. Gan and D. Schlenk, J. Chromatogr. B, 878, 1277 (2010).
  10. L. Li, S.S. Zhou, L.X. Jin, C. Zhang and W.P. Li, J. Chromatogr. B, 878, 1264 (2010).
  11. Y.H. Zhu, Z.R. Wang and B.Q. Li, Encyclopedia of Agricultural Chemistry (2006).
  12. P. Schmitt, A.W. Garrison, D. Freitag and A. Kettrup, J. Chromatogr. A, 792, 419 (1997).
  13. E. Yashima, J. Chromatogr. A, 906, 105 (2001).
  14. Y. Okamoto and E. Yashima, Angew. Chem. Int. Ed., 37, 1020 (1998).
  15. P. Wang, S.R. Jiang and Z.Q. Zhou, J. Agric. Food Chem., 54, 1577 (2006).
  16. E.N. Shapovalova, O.A. Shpigun, L.M. Nesterova and M.Y. Belov, J. Anal. Chem., 59, 255 (2004).
  17. Y. Zhou, L. Li, K.D. Lin, X.P. Zhu and W.P. Liu, Chirality, 21, 421 (2009).
  18. J. Qiu, S.H. Dai, S.M. Yang, T.T. Chai and M. Bie, Chirality, 23, 479 (2011).
  19. T. Zhang, D. Nguyen and P. Franco, J. Chromatogr. A, 1217, 1048 (2010).
  20. A. Berthod, Anal. Chem., 78, 2093 (2006).
  21. L.M. Peng, S. Jayapalan, B. Chankvetadze and T. Farkas, J. Chromatogr. A, 1217, 6942 (2010).
  22. R.J. Smith, D.R. Taylor and S.M. Wilkins, J. Chromatogr. A, 697, 591 (1995).
  23. A. Péter, E. Vékes and D.W. Armstrong, J. Chromatogr. A, 958, 89 (2002).
  24. O. Gyllenhaal and M. Stefansson, Chirality, 17, 257 (2005).
  25. T. O'Brien, L. Crocker, R. Thompson, K. Thompsom, P. Toma, D. Conlon, B. Feibush, C. Moeder, G. Bicker and N. Grinberg, Anal. Chem., 69, 1999 (1997).
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