KSBB Journal

The Korean Society for Biotechnology and Bioengineering (한국생물공학회)
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Effect of Mobile Phase Additive on Enantiomer Resolution for Chiral Amines on Polysaccharide-derived Chiral Stationary Phases by High Performance Liquid Chromatography

고성능 액체크로마토그래피의 다당유도체를 기초로 한 키랄 고정상에서 이동상 첨가제가 키랄 아민의 광학분리에 미치는 영향

  • 백만정 (순천대학교 약학대학 약학과) ;
  • 윤혜란 (덕성여자대학교 약학대학 약학과) ;
  • 이원재 (조선대학교 약학대학 약학과)
  • Received : 2014.04.08
  • Accepted : 2014.06.24
  • Published : 2014.06.30
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Abstract

Chromatographic enantiomer resolution of chiral amines was performed on several covalently immobilized and coated chiral stationary phases (CSPs) based on polysaccharide derivatives under the mobile phase conditions containing base or acid or acid/base additive. The chromatographic parameters including separation factors and capacity factors were greatly influenced by the nature of the mobile phase containing base or acid or salt additive as well as the used CSPs. When 0.05% triethylamine/0.05% trifluoroacetic acid as an additive in the mobile phase was used on all CSPs in this study, the greatest enantiomer resolution was observed except for Chiralpak AD. Also, it was shown that the change of base additive into acid or salt in the mobile phase may directly affect chiral recognition mechanisms between the chiral selectors and analytes occurring during enantiomer separation, resulting in the change of elution orders.

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References

  1. G. Subramanian, (Ed.) (2001) Chiral Separation Techniques: A practical approach. 2nd revised ed., VCH, Weinheim.
  2. W. Lee (2009) The application of chiral HPLC columns for enantiomer separation of chiral drugs. Yakhak Hoeji 53: 60-68.
  3. Application Guide for Chiral HPLC selection, 4th ed., (2008) Daicel Chemical Industries, Ltd.
  4. Li, Y. H. and W. Lee (2005) Liquid chromatographic enantiomer resolution of N-fluorenylmethoxycarbonyl $\alpha$-amino acids and their ester derivatives on polysaccharide-derived chiral stationary phases. J. Sep. Sci. 30: 2057-2060.
  5. Jin, J. Y., W. Lee, and C. S. Baek (2008) Enantiomer resolution of non-steroidal anti-inflammatory drugs on chiral stationary phases derived from polysaccharide derivatives. Chin. J. Anal. Chem. 36: 1207-1211. https://doi.org/10.1016/S1872-2040(08)60067-5
  6. Jin, J. Y., S. K, Bae, and W. Lee (2009) Comparative studies between covalently immobilized and coated chiral stationary phases based on polysaccharide derivatives for enantiomer separation of N-protected $\alpha$-amino acids and their ester derivatives. Chirality 21: 871-877. https://doi.org/10.1002/chir.20680
  7. Strigham, R. W. and Y. K. Ye (2006) Chiral separation of amines by high-performance liquid chromatography using polysaccharide stationary phases and acidic additives. J. Chromatogr. A 1101: 86-93. https://doi.org/10.1016/j.chroma.2005.09.065
  8. Ye, Y. K. and R. W. Strigham (2006) The effect of acidic and basic additives on the enantioseparation of basic drugs using polysaccharide-based chiarl stationary phases. Chirality 18: 519-530. https://doi.org/10.1002/chir.20287
  9. Tang, Y., W. L. Zielinski, and H. M. Bigott (1998) Separation of nicotine and nornicotine enantiomers via normal phase HPLC on derivatized cellulose chiarl stationary phases. Chirality 10: 364-369. https://doi.org/10.1002/(SICI)1520-636X(1998)10:4<364::AID-CHIR13>3.0.CO;2-Y
  10. S. Caccamese, S. S. Bianca, and G. T. Carter (2007) Direct highperformance liquid chromatographic separation of the enantiomers of an aromatic amine and four aminoalchols using polysaccharide chiral stationary phases and acidic additive. Chirality 21: 647-653.
  11. Xu, W. J., J. Y. Jin, and W. Lee (2011) Enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives on coated and covalently bonded chiral stationary phases based on polysaccharide derivatives by high performance liquid chromatography. Kor. Soc. Biotech. Bioeng. J. 26: 323-327. https://doi.org/10.7841/ksbbj.2011.26.4.323