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DOI QR Code

The Effect of Mobile Phase and Dissolving Solvent on the Enantiomer Separation Using a Covalently Immobilized Chiral Column Derived from Polysaccharide Derivative

다당유도체로 공유결합된 카이랄 칼럼에서 이동상과 분석물질의 용매가 거울상 이성질체의 광학분할에 미치는 영향

  • 황호 (조선대학교 약학대학 약학과) ;
  • 이범규 (조선대학교 자연과학대학 화학과) ;
  • 백채선 (조선대학교 약학대학 약학과) ;
  • 이원재 (조선대학교 약학대학 약학과)
  • Published : 2009.04.20

Abstract

Liquid chromatographic enantiomer separation of N-tert-butoxycarbonyl (BOC) $\alpha$-amino acids and their ethyl esters was performed on covalently immobilized chiral column (Chiralpak IC) derived from polysaccharide derivative. The solvent versatility of the covalently immobilized Chiralpak IC in enantiomer separation of N-BOC $\alpha$-amino acid ethyl ester derivatives was shown and the chromatographic parameters of their enantioselectivities and resolution factors were greatly influenced by the nature of the mobile phase. Also the effect on the dissolving solvent for these analytes on the enantiomer separation using the same mobile phase and the examples of preparative enantiomer separation on analytical column were shown.

Keywords

Enantiomer separation;Chiral column;Amino acid;Chiralpak IC;Liquid chromatography

References

  1. Yashima, E. J. Chromatogr. A, 2001, 906, 105-125. https://doi.org/10.1016/S0021-9673(00)00501-X
  2. Okamoto, Y.; Yashima, E. Angew. Chem. Int. Ed.,1998, 37, 1020-1043. https://doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1020::AID-ANIE1020>3.0.CO;2-5
  3. Application guide for chiral HPLC selection; 3rd Ed., Daicel Chemical Industries, Ltd.
  4. Ali, I.; Aboul-Enein, H. Y. J. Sep. Sci., 2006, 29, 762-769. https://doi.org/10.1002/jssc.200500372
  5. Ghanem, A. J. J. Sep. Sci., 2007, 30, 1019-1028. https://doi.org/10.1002/jssc.200600357
  6. Zhang, T.; Kientzy, C.; Franco, P.; Ohnishi, A.; Kagamihara, Y.; Kurosawa, H. J. Chromatogr. A, 2005, 1075, 65-75. https://doi.org/10.1016/j.chroma.2005.03.116
  7. Zhang, T.; Nguyen, D.; Franco, P.; Murakami, T.;Ohnishi, A. ; Kurosawa, H. Anal. Chim. Acta, 2006, 557, 221-228. https://doi.org/10.1016/j.aca.2005.10.017
  8. Jin, J. Y.; Lee, W. Bull. Kor. Chem. Soc., 2008, 29, 491-493. https://doi.org/10.5012/bkcs.2008.29.2.491
  9. Jin, J. Y.; Lee, W.; Park, J. H.; Ryoo, J. J. J. Liq. Chrom. & Rel. Tech., 2006, 29, 1793-1801. https://doi.org/10.1080/10826070600717007
  10. Jin, J. Y.; Bae, S. K.; Lee, W. Chirality, 2009, in press.
  11. CHIRALPAK IC, Analytical HPLC applications;Daicel Chemical Industries, Ltd, 2007.
  12. Zhang, T.; Nguyen, D.; Franco, P.; Isobe, Y.;Michishita, T.; Murakami, T. J. Pharma. Biomed. Anal., 2008, 46, 882-891. https://doi.org/10.1016/j.jpba.2007.06.008
  13. Zhang, T.; Nguyen, D.; Franco, P. J. Chromatogr. A, 2008, 1191, 214-222. https://doi.org/10.1016/j.chroma.2007.12.026
  14. Franco, P.; Zhang, T. J. Chromatogr. B, 2008, 875, 48-56. https://doi.org/10.1016/j.jchromb.2008.06.051
  15. Jin, J. Y.; Lee, W.; Baek, C. S. Chin. J. Anal. Chem., 2008, 36, 1207-1211. https://doi.org/10.1016/S1872-2040(08)60067-5
  16. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 3rd Ed., John Wiley & Sons: New York, 1999.
  17. Bodansky, M.; Bodansky, A. The Practice of Peptide Synthesis; Springer: New York, 1984.