DOI QR코드

DOI QR Code

The Influence of Temperature, Ultrasonication and Chiral Mobile Phase Additives on Chiral Separation: Predominant Influence of β-Cyclodextrin Chiral Mobile Phase Additive Under Ultrasonic Irradiation

  • Lee, Jae Hwan (Department of Science Education, Graduate School, Kyungpook National University) ;
  • Ryoo, Jae Jeong (Department of Science Education, Graduate School, Kyungpook National University)
  • 투고 : 2012.07.26
  • 심사 : 2012.09.28
  • 발행 : 2012.12.20

초록

This paper introduces a technique for resolving amino acids that combines the advantages of the conventional CSP (chiral stationary phase) method with the CMPA (chiral mobile phase additive) method. A commercially available chiral crown ether column, CROWNPAK CR(+), was used as the CSP and three cyclodextrins (${\beta}$-CD, ${\gamma}$-CD, HP-${\beta}$-CD) were used as the mobile phase additives. Chromatographic resolution was performed at $25^{\circ}C$ and $50^{\circ}C$ with or without sonication. A comparison of the chromatographic results under ultrasonic conditions with those under non-ultrasonic conditions showed that ultrasound decreased the elution time and enantioselectivity at all temperatures. In the case of the ${\beta}$-CD mobile phase additive, the elution time and enantioselectivity under ultrasonic condition were significantly higher than under non-sonic condition at all temperatures. Commercially available Chiralpak AD, Whelk-O2 and Pirkle 1-J columns were used as CSPs to examine more meticulously the effects of ultrasonication and temperature on the optical resolution. The optical resolution of some chiral samples analyzed at $25^{\circ}C$ and $50^{\circ}C$ with or without sonication was compared. As in the previous case, the enantioselectivity was lower at $25^{\circ}C$ but similar enantioselectivity was observed at $50^{\circ}C$.

키워드

참고문헌

  1. Pirkle, W. H.; House, D. W.; Finn, J. M. Chromatographia 1980, 143, 2.
  2. Hinze, W. H.; Riehl, T. E.; Amstrong, D. W. Anal. Chem. 1979, 51, 33. https://doi.org/10.1021/ac50037a727
  3. Sun, P.; Wang, C.; Breitbach, Z. S.; Zhang, Y.; Armstrong, D. W. Anal. Chem. 2009, 81, 10215. https://doi.org/10.1021/ac902257a
  4. Hare, P. E.; Gil-Av, E. Science 1979, 204, 1226. https://doi.org/10.1126/science.36662
  5. Ward, T. J.; Ward, K. D. Anal. Chem. 2012, 84, 626. https://doi.org/10.1021/ac202892w
  6. Keith, J.; Duff, K. J.; Gray, H. L.; Gray, R. J.; Bahler, C. C. Chirality 1993, 5, 201. https://doi.org/10.1002/chir.530050402
  7. Sun, Q.; Olesik, S. V. J. Chromatography B 2000, 745, 159. https://doi.org/10.1016/S0378-4347(00)00267-X
  8. Okada, T. J. Chromatography A 1998, 793, 365. https://doi.org/10.1016/S0021-9673(97)00903-5
  9. Oszwaldowski, S.; Okada, T. J. Chromatography A 1999, 850, 9. https://doi.org/10.1016/S0021-9673(99)00492-6
  10. Ryoo, J. J.; Song, Y. A.; Jeong, Y. H.; Hyun, M. H.; Park, J. H.; Lee, W. Bull. Korean Chem. Soc. 2006, 27, 637. https://doi.org/10.5012/bkcs.2006.27.5.637
  11. Krstulovic, A. M.; Colin, H.; Guiochon, G. Anal. Chem. 1982, 54, 2438. https://doi.org/10.1021/ac00251a009
  12. Cho, Y. J.; Choi, H. J.; Hyun, M. H. J. Chromatography A 2008, 1191, 193. https://doi.org/10.1016/j.chroma.2007.11.019
  13. Krefting, D.; Mettin, R.; Lauterborn, W. Ultrason. Sonochem. 2004, 11, 119. https://doi.org/10.1016/j.ultsonch.2004.01.006
  14. Maisonhaute, E.; Prado, C.; White, P. C. Ultrason. Sonochem. 2002, 9, 297. https://doi.org/10.1016/S1350-4177(02)00089-5

피인용 문헌

  1. alkaloid based stationary phase: Enantiorecognition mechanism and release studies vol.37, pp.19, 2014, https://doi.org/10.1002/jssc.201400630
  2. Separation of 3-Biphenylcarboxylic Acid and 4-Biphenylcarboxylic Acid Isomers with Chromatographic Column of Solid β-Cyclodextrin vol.37, pp.6, 2016, https://doi.org/10.1002/bkcs.10792
  3. Racemic drug resolution: a comprehensive guide vol.8, pp.42, 2016, https://doi.org/10.1039/C6AY02015A
  4. Ultrasound-Controlled Chiral Separation of Four Amino Acids and 2,2,2-Trifluoro-1-(9-anthryl)ethanol vol.40, pp.2, 2019, https://doi.org/10.1002/bkcs.11659