Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

  • Yoon, Hoe-Jin (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Jung, Hein (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Ahn, Yun-Soo (Aminolux R&D Center) ;
  • Nandhakumar, Raju (Department of Chemistry, Karunya University) ;
  • Kim, Jun-Soo (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Kim, Kwan-Mook (Department of Chemistry and Nano Science (BK21), Ewha Womans University)
  • Received : 2012.01.18
  • Accepted : 2012.02.23
  • Published : 2012.05.20
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Abstract

2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

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