Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Deracemization of Racemic Amino Acids Using (R)- and (S)-Alanine Racemase Chiral Analogues as Chiral Converters

  • Received : 2014.03.10
  • Accepted : 2014.03.19
  • Published : 2014.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

Experimental

The chemicals used in this study were purchased from Aldrich (Milwaukee, WI) or Fluka (Switzerland) and were analytical-reagent grade. (R)- and (S)-ARCA were provided by Aminologics Company (Sungnam, Korea). The amino acid stereoconversion samples using (R)- and (S)-ARCA were prepared as described previously.2-5 HPLC studies were carried out using a Breeze system (Waters, Milford, MA) equipped with a binary pump (Waters model 1525), an autosampler, and a dual absorbance detector (Waters 2487 detector). Capcell Pak C18 UG 120 (250 × 4.6 mm I.D., 5 μm) (Shiseido Company, Japan) for diastereomer analysis and ChiroSil SCA (250 × 4.6 mm I.D., 5 μm) (RS Tech, Daejon, Korea) based on (−)-18-C-6-TA for enantiomer analysis were used.10,11

References

  1. Turner, N. J. Curr. Opin. Chem. Biol. 2004, 8, 114. https://doi.org/10.1016/j.cbpa.2004.02.001
  2. Park, H.-J., Nandhakumar, R.; Hong, J.; Ham, S.; Chin, J.; Kim, K. M. Chem. Eur. J. 2008, 14, 9935. https://doi.org/10.1002/chem.200801036
  3. Nandhakumar, R.; Ryu, J.; Park, H.-J.; Tang, L.; Choi, S.; Kim, K. M. Tetrahedron 2008, 64, 7704. https://doi.org/10.1016/j.tet.2008.06.029
  4. Tang, L.; Ga, H.; Kim, J.; Choi, S.; Nandhakumar, R.; Kim, K. M. Tetrahedron Lett. 2008, 49, 6914. https://doi.org/10.1016/j.tetlet.2008.09.117
  5. Park, H.-J.; Kim, K. M.; Lee, A.; Ham, S.; Nam, W.; Chin, J. J. Am. Chem. Soc. 2007, 129, 1518. https://doi.org/10.1021/ja067724g
  6. Subramanian, G., Ed.; Chiral Separation Techniques: A Practical Approach; Wiley-VCH: Weinheim, 2001.
  7. Eliel, E. L.; Wilen S. H.; Mandor, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994.
  8. Bang, E.; Jin, J. Y.; Hong, J. H.; Kang, J. S.; Lee, W.; Lee, W. Bull. Korean Chem. Soc. 2012, 33, 3481. https://doi.org/10.5012/bkcs.2012.33.10.3481
  9. Lee, W.; Bang, E.; Lee, W. Chromatographia 2003, 57, 457. https://doi.org/10.1007/BF02492541
  10. Paik, M.-J.; Kang, J. S.; Huang, B.-S.; Carey, J. R.; Lee, W. J. Chromatogr. A 2013, 1274, 1. https://doi.org/10.1016/j.chroma.2012.11.086
  11. Jin, J. Y.; Lee, W.; Hyun, M. H. J. Liq. Chrom. & Rel. Technol. 2006, 29, 841. https://doi.org/10.1080/10826070500531102