Bulletin of the Korean Chemical Society

  • 제34권10호
  • /
  • Pages.2978-2982
  • /
  • 2013
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Resolution of Tocainide and Its Analogues on a Doubly Tethered N-CH3 Amide Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

  • Lee, Kyu Jung (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Tak, Kyung Mi (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Hyun, Myung Ho (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
  • 투고 : 2013.06.07
  • 심사 : 2013.07.15
  • 발행 : 2013.10.20
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초록

A doubly tethered $N-CH_3$ amide chiral stationary phase (CSP 4) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of an antiarrythmic agent, tocainide, and its analogues and the chromatographic resolution results were compared with those on a singly tethered N-H amide CSP (CSP 1), a singly tethered $N-CH_3$ amide CSP (CSP 2) and a doubly tethered N-H amide CSP (CSP 3) under an identical aqueous mobile phase condition. CSP 4 was found to be generally better than other CSPs in terms of the separation factors (${\alpha}$) and resolutions (RS). The retention times of analytes denoted by the retention factors ($k_1$) on CSP 4 were quite long compared to those on other CSPs because of the improved lipophilicity of CSP 4. The long retention times of analytes on CSP 4 were successfully controlled by the addition of a small amount of ammonium acetate to aqueous mobile phase without hurting the chiral recognition efficiency. The variation of the content and type of organic and acidic modifier in aqueous mobile phase was found not to change the chiral recognition efficiency significantly.

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참고문헌

  1. Francotte, E. R. J. Chromatogr. A 2001, 906, 379. https://doi.org/10.1016/S0021-9673(00)00951-1
  2. Andersson, S.; Allenmark, S. G. J. Biochem. Biophys. Methods 2002, 54, 11. https://doi.org/10.1016/S0165-022X(02)00126-4
  3. Lammerhofer, M. J. Chromatogr. A 2010, 1217, 814. https://doi.org/10.1016/j.chroma.2009.10.022
  4. Hyun, M. H.; Han, S. C.; Lipshutz, B. H.; Shin, Y.-J.; Welch, C. J. J. Chromatogr. A 2001, 910, 359. https://doi.org/10.1016/S0021-9673(00)01230-9
  5. Hyun, M. H.; Cho, Y. J.; Kim, J. A.; Jin, J. S. J. Chromatogr. A 2003, 984, 163. https://doi.org/10.1016/S0021-9673(02)01833-2
  6. Hyun, M. H. J. Sep. Sci. 2003, 26, 242. https://doi.org/10.1002/jssc.200390030
  7. Hyun, M. H.; Kim, D. H. Chirality 2004, 16, 294. https://doi.org/10.1002/chir.20038
  8. Hyun, M. H.; Cho, Y. J. J. Sep. Sci. 2005, 28, 31. https://doi.org/10.1002/jssc.200401919
  9. Hyun, M. H.; Kim, D. H.; Cho, Y. J.; Jin, J. S. J. Sep. Sci. 2005, 28, 421. https://doi.org/10.1002/jssc.200401951
  10. Hyun, M. H. Bull. Kor. Chem. Soc. 2005, 26, 1153. https://doi.org/10.5012/bkcs.2005.26.8.1153
  11. Hyun, M. H.; Song, Y.; Cho, Y. J.; Kim, D. H. J. Chromatogr. A 2006, 1108, 208. https://doi.org/10.1016/j.chroma.2006.01.012
  12. Hyun, M. H. J. Sep. Sci. 2006, 29, 750. https://doi.org/10.1002/jssc.200500431
  13. Choi, H. J.; Hyun, M. H. J. Liq. Chromatogr. Rel. Technol. 2007, 30, 853. https://doi.org/10.1080/10826070701191136
  14. Hyun, M. H.; Han, S. C.; Choi, H. J.; Kang, B. S.; Ha, H. J. J. Chromatogr. A 2007, 1138, 169. https://doi.org/10.1016/j.chroma.2006.10.048
  15. Hyun, M. H. In Comprehensive Chirality, Carreira, E. M.; Yamamoto, H., Eds.; Elsevier: Amsterdam, Netherlands, 2012; Vol. 8, p 263.
  16. Hyun, M. H.; Jin, J. S.; Lee, W. J. Chromatogr. A 1998, 822, 155. https://doi.org/10.1016/S0021-9673(98)00606-2
  17. Hyun, M. H.; Jin, J. S.; Koo, H. J.; Lee, W. J. Chromatogr. A 1999, 837, 75. https://doi.org/10.1016/S0021-9673(99)00100-4
  18. Hyun, M. H.; Han, S. C.; Koo, H. J.; Lee, W. Chromatographia 2000, 52, 473. https://doi.org/10.1007/BF02535722
  19. Hyun, M. H.; Cho, Y. J.; Jin, J. S. J. Sep. Sci. 2002, 25, 648. https://doi.org/10.1002/1615-9314(20020701)25:10/11<648::AID-JSSC648>3.0.CO;2-D
  20. Hyun, M. H.; Tan, T.; Cho, Y. J. J. Liq. Chromatogr. Rel. Technol. 2004, 27, 1671. https://doi.org/10.1081/JLC-120037363
  21. Conrad, U.; Chankvetadze, B.; Scriba, G. K. E. J. Sep. Sci. 2005, 28, 2275. https://doi.org/10.1002/jssc.200500193
  22. Berkecz, R.; Sztojkov-Ivanov, A.; Ilisz, I.; Forro, E.; Fulop, F.; Hyun, M. H.; Peter, A. J. Chromatogr. A 2006, 1125, 138. https://doi.org/10.1016/j.chroma.2006.06.064
  23. Lee, S. J.; Cho, H. S.; Choi, H. J.; Hyun, M. H. J. Chromatogr. A 2008, 1188, 318. https://doi.org/10.1016/j.chroma.2008.02.102
  24. Steffeck, R. J.; Zelechonok, Y.; Gahm, K. H. J. Chromatogr. A 2002, 947, 301. https://doi.org/10.1016/S0021-9673(01)01604-1
  25. Zhang, D.; Famei, L; Kim, D. H.; Choi, H. J. Hyun, M. H. J. Chromatogr. A 2005, 1083, 89. https://doi.org/10.1016/j.chroma.2005.06.038
  26. Hyun, M. H.; Tan, G.; Xue, J. Y. J. Chromatogr. A 2005, 1097, 188. https://doi.org/10.1016/j.chroma.2005.10.036
  27. Tan, G.; Xue, J. Y.; Hyun, M. H. J. Sep. Sci. 2006, 29, 1407. https://doi.org/10.1002/jssc.200600026
  28. Choi, H. J.; Park, Y. J.; Hyun, M. H. J. Chromatogr. A 2007, 1164, 235. https://doi.org/10.1016/j.chroma.2007.07.025
  29. Lee, A.; Choi, H. J.; Hyun, M. H. Chirality 2010, 22, 693.
  30. Lee, A.; Choi, H. J.; Jin, K. B.; Hyun, M. H. J. Chromatogr. A 2011, 1218, 4071. https://doi.org/10.1016/j.chroma.2011.04.088
  31. Hyun, M. H.; Min, H. J.; Cho, Y. J. Bull. Korean Chem. Soc. 2003, 24, 911. https://doi.org/10.5012/bkcs.2003.24.7.911
  32. Jamali, F.; Mehvar, R.; Pasutto, F. M. J. Pharm. Sci. 1989, 78, 695. https://doi.org/10.1002/jps.2600780902
  33. Antonsson, A.-M.; Gyllenhaal, O.; Kylberg-Hanssen, K.; Johansson, L.; Vessman, J. J. Chromatogr. Biomed. Appl. 1984, 308, 181. https://doi.org/10.1016/0378-4347(84)80207-8
  34. Kim, H. J.; Choi, H. J.; Hyun, M. H. Bull. Korean Chem. Soc. 2010, 31, 678. https://doi.org/10.5012/bkcs.2010.31.03.678
  35. Hyun, M. .; Cho, Y. J.; Song, Y.; Choi, H. J.; Kang, B. S. Chirality 2007, 19, 74. https://doi.org/10.1002/chir.20346

피인용 문헌

  1. Development of HPLC Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and Their Applications vol.27, pp.9, 2015, https://doi.org/10.1002/chir.22484