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Chromatographic Enantiomer Separation and Determination of Optical Purity for α-Amino Acid Esters as 9-Anthraldimine Derivatives Using Polysaccharide Based Chiral Columns
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  • Journal title : KSBB Journal
  • Volume 26, Issue 2,  2011, pp.139-142
  • Publisher : Korean Society for Biotechnology and Bioengineering
  • DOI : 10.7841/ksbbj.2011.26.2.139
 Title & Authors
Chromatographic Enantiomer Separation and Determination of Optical Purity for α-Amino Acid Esters as 9-Anthraldimine Derivatives Using Polysaccharide Based Chiral Columns
Huang, Hu; Jin, Jing-Yu; Lee, Won-Jae;
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 Abstract
The chromatographic enantiomer separation of 9-anthraldimine derivatives of -amino acid methyl and ethyl esters on four polysaccharide based chiral columns was performed. The 9-anthraldehyde Schiff base derivatives of - amino acid esters were readily synthesized by stirring the - amino acid ester hydrochloride salts with 9-anthraldehyde in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene as a base and anhydrous . Chiralcel OD or Chiralcel OD-H showed the greatest enantiomer resolution of 9-anthraldimine derivatives of -amino acid methyl and ethyl esters. The L-enantiomers of all the analytes were preferentially retained on Chiralcel OD or Chiralcel OD-H. This analytical method was applied in the determination of optical purities of several commercially available D- or L--amino acid methyl esters.
 Keywords
Enantiomer separation;Amino acid ester;Chiral column;Optical purity;
 Language
Korean
 Cited by
1.
고성능 액체 크로마토그래피에 의한 다당 유도체를 기초로 한 흡착되거나 공유결합된 키랄 고정상에서 키랄 아미노 알코올의 안트르알디민 유도체의 광학분리,서문준;김경옥;이원재;

KSBB Journal, 2011. vol.26. 4, pp.323-327 crossref(new window)
2.
아미노산 에스테르의 벤조피논 이민 유도체의 액체 크로마토그래피의 광학분리,윤원남;서문준;황호;이원재;

KSBB Journal, 2012. vol.27. 3, pp.167-171 crossref(new window)
3.
키랄 컬럼을 사용한 아미노산 에스테르의 니트로벤조옥사디아졸 유도체의 광학분리,윤원남;김지연;이원재;

KSBB Journal, 2013. vol.28. 6, pp.423-427 crossref(new window)
1.
Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns, KSBB Journal, 2013, 28, 6, 423  crossref(new windwow)
2.
Liquid Chromatographic Resolution of α-Amino Acid Esters as Benzophenone Imine Derivatives, KSBB Journal, 2012, 27, 3, 167  crossref(new windwow)
 References
1.
Subramanian, G. (Ed.) (2001) Chiral Separation Techniques: A practical approach second revised ed., VCH, Weinheim.

2.
Beesley, T. E. and R. P. W. Scott (Ed.) (1998) Chiral Chromatography, New York, John Wiley & Sons.

3.
Greene, T. W. and P. G. M. Wuts (1999) Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, New York.

4.
Pu, L. and H.-B. Yu (2001) Catalytic asymmetric organozinc additions to carbonyl compounds. Chem. Rev. 101: 757-824. crossref(new window)

5.
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. crossref(new window)

6.
Application Guide for Chiral HPLC selection, 4th ed. (2008) Daicel Chemical Industries, Ltd.

7.
Hyun, M. H., J. S. Jin, and W. Lee (1998) Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether, J. Chromatogr. A. 822: 155-161. crossref(new window)

8.
Kim, B.-H. and W. Lee (1999) Direct liquid chromatographic enantiomer separation of N-tert-butoxycarbonyl and benzyloxycarbonyl ${\alpha}$-amino acids using polysaccharide derived chiral stationary phases. J. Liq. Chrom. & Rel. Tech. 22: 523-530. crossref(new window)

9.
Jin, J. Y., W. Lee, J. H. Park, and J. J. Ryoo (2006) Covalently bonded and coated chiral stationary phases derived from polysaccharide derivatives for enantiomer separation of Nfluorenylmethoxycarbonyl ${\alpha}$-amino acids with fluorescence detection. J. Liq. Chrom. & Rel. Tech. 29: 1793-1801. crossref(new window)

10.
Jin, J. Y., W. Lee, J. H. Park, and J. J. Ryoo (2007) Liquid chromatographic enantiomer separation of N-phthaloyl protected ${\alpha}$-amino acids on coated and immobilized chiral stationary phases derived from polysaccharide derivatives. J. Liq. Chrom. & Rel. Tech. 30: 1-9. crossref(new window)

11.
Jin, J. Y., W. Lee, and C.-S. Baek (2008) Enantiomer resolution of nonsteroidal anti-inflammatory drugs on chiral stationary phases derived from polysaccharide derivatives. Chin. J. Anal. Chem. 36: 1207-1211. crossref(new window)

12.
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. crossref(new window)