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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

고성능 액체 크로마토그래피에 의한 다당 유도체를 기초로 한 흡착되거나 공유결합된 키랄 고정상에서 키랄 아미노 알코올의 안트르알디민 유도체의 광학분리

  • 서문준 (조선대학교 약학대학 약학과) ;
  • 김경옥 (조선대학교 약학대학 약학과) ;
  • 이원재 (조선대학교 약학대학 약학과)
  • Received : 2011.05.19
  • Accepted : 2011.08.02
  • Published : 2011.08.30

Abstract

The convenient derivatization method of chiral amino alcohols as 9-anthraldimine Schiff base derivatives for chiral resolution was developed and the liquid chromatographic enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives was investigated on several coated and covalently bonded polysaccharide-derived chiral stationary phases (CSPs). In general, the performance of Chiralcel OD-H (or Chiralcel OD) (${\alpha}$ = 1.24-2.89), the coated CSP derived from cellulose derivative was superior to the other CSPs for resolution of 9-anthraldimine derivatives of several amino alcohols. The results of enantioseparation depending on the structure of 9-anthraldimine analytes like the steric bulky group and the polar moiety etc were discussed. The analytical method was applied to measure the enantiomeric purity of commercially available chiral amino alcohols. It is expected that the convenient analytical method will be very efficient for determination of enantiomeric purity of amino alcohols as 9-anthraldimine Schiff base derivatives with strong UV absorption.

Keywords

Acknowledgement

Supported by : 조선대학교

References

  1. Challener, C. A. (Ed.) (2002) Chiral Drugs. Ashgate Publishing, Aldershot, UK.
  2. Subramanian, G. (Ed.) (2001) Chiral Separation Techniques: A Practical Approach. Wiley-VCH, Weinheim, Germany.
  3. Huang, H., J. Y. Jin, and W. Lee (2011) Chromatographic enantiomer separation and determination of optical purity for α-amino acid esters as 9-anthraldimine derivatives using polysaccharide based chiral columns. Kor. Soc. Biotech. Bioeng. J. 26: 139-142.
  4. Duchateau, A. L. L., J. J. Guns, R. G. R. Kubben, and A. F. P. van Tilburg (1994) High-performance liquid chromatography of diamine enantiomers as Schiff bases on a chiral stationary phase. J. Chromatogr. A. 664: 169-176. https://doi.org/10.1016/0021-9673(94)87004-7
  5. Greene, T. W. and P. G. M. Wuts (1999) Protective Groups in Organic Synthesis. 3rd ed., John Wiley & Sons, New York, USA.
  6. Application Guide for Chiral HPLC selection, 4th ed., (2008) Daicel Chemical Industries, Ltd.
  7. Thunberg, L., J. Hashemi, and S. Andersson (2008) Comparative study of coated and immobilized polysaccharide-based chiral stationary phases and their applicability in the resolution of enantiomers. J. Chromatogr. B. 875: 72-80. https://doi.org/10.1016/j.jchromb.2008.07.044
  8. Li, Y. H. and W. Lee (2005) Liquid chromatographic enantiomer resolution of N-fluorenylmethoxycarbonyl α-amino acids and their ester derivatives on polysaccharide-derived chiral stationary phases. J. Sep. Sci. 30: 2057-2060.
  9. Jin, J. Y., W. Lee, J. H. Park, and J. J. Ryoo (2007) Liquid chromatographic enantiomer separation of N-phthaloyl protected α-amino acids on coated and immobilized chiral stationary phases derived from polysaccharide derivatives. J. Liq. Chrom. & Rel. Tech. 30: 1-9. https://doi.org/10.1080/10826070601034170
  10. Jin, J. Y. and W. Lee (2008) Enantiomer separation of N-protected α-amino acids on covalently immobilized cellulose tris (3,5- chlorophenylcarbamate) chiral stationary phase in HPLC, Bull. Kor. Chem. Soc. 29: 491-493. https://doi.org/10.5012/bkcs.2008.29.2.491
  11. 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

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