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http://dx.doi.org/10.7841/ksbbj.2011.26.2.139

Chromatographic Enantiomer Separation and Determination of Optical Purity for α-Amino Acid Esters as 9-Anthraldimine Derivatives Using Polysaccharide Based Chiral Columns  

Huang, Hu (College of Pharmacy, Chosun University)
Jin, Jing-Yu (College of Pharmacy, Chosun University)
Lee, Won-Jae (College of Pharmacy, Chosun University)
Publication Information
KSBB Journal / v.26, no.2, 2011 , pp. 139-142 More about this Journal
Abstract
The chromatographic enantiomer separation of 9-anthraldimine derivatives of ${\alpha}$-amino acid methyl and ethyl esters on four polysaccharide based chiral columns was performed. The 9-anthraldehyde Schiff base derivatives of ${\alpha}$- amino acid esters were readily synthesized by stirring the ${\alpha}$- 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 $MgSO_4$. Chiralcel OD or Chiralcel OD-H showed the greatest enantiomer resolution of 9-anthraldimine derivatives of ${\alpha}$-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-${\alpha}$-amino acid methyl esters.
Keywords
Enantiomer separation; Amino acid ester; Chiral column; Optical purity;
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