, Volume 17, Issue 1, pp 23–26 | Cite as

Determination of the enantiomeric purity of oxfenicine by high-performance liquid chromatography

  • M. W. Coleman


Reaction of the methyl esters of the α-amino acids, R-(−)-, and S-(+)-4-hydroxyphenylglycine (oxfenicine) with the enantiomerically pure acid anhydride of R-(+)-1-methoxy-1-trifluoromethyl-phenylacetic acid (i.e. R-(+)-MTPA) yields diastereoisomeric amides which are separable by high-performance liquid chromatography (HPLC). The ratios of the diastereoisomeric amides may be measured chromatographically and are shown to correspond to the enantiomeric purities of the amino acids. This method is particularly well suited for detecting low levels of an enantiomeric impurity in α-amino acids which possess a base labile α-methine hydrogen atom.

Key Words

Enantiomeric purity α-Amino acids Oxfenicine High-performance liquid chromatography 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. [1]
    K. J. Blackburn, R. A. Burges, D. G. Gardiner, M. Morville, M. G. Page, Brit. J. Pharmacol. 443P (1979).Google Scholar
  2. [2]
    I. T. Barnish, P. E. Cross, J. C. Danilewicz, R. P. Dickinson, D. A. Stopher, J. Med. Chem.,24, 399 (1981).Google Scholar
  3. [3]
    G. Helmchen, R. Ott, K. Sauber Tetrahedron Lett., 3873 (1972).Google Scholar
  4. [4]
    H. Furukawa, E. Sakakibara, A. Kamei, K. Ito, Chem. Pharm. Bull. (Japan),23, 1625 (1975).Google Scholar
  5. [5]
    J. Goto, M. Hasegawa, S. Nakamura, K. Shimada, T. Nambara, Chem. Pharm. Bull (Japan),25, 847 (1977).Google Scholar
  6. [6]
    H. Furukawa, Y. Mori, Y. Takeuchi, K. Ito, J. Chromatog.,136, 428 (1977).Google Scholar
  7. [7]
    T. Nambara, S. Ikegawa, M. Hasegawa, J. Goto Anal. Chim. Acta,101, 111 (1978).Google Scholar
  8. [8]
    J. Hermansson, B. Wiese, Chromatographia,14, 529 (1981).Google Scholar
  9. [9]
    T. Kinoshita, Y. Kasahara, N. Nimura J. Chromatogr.,210, 77 (1981).Google Scholar
  10. [10]
    J. Boué, R. Audebert, C. Quivoron, J. Chromatog.,204, 185 (1981).Google Scholar
  11. [11]
    J. C. Clark, G. H. Phillipps, M. R. Stear, J. Chem. Soc., PerkinI, 475 (1976).Google Scholar
  12. [12]
    M. Raban, K. Mislow, in: Topics in Stereochemistry, (Editors: E. L. Eliel and N. A. Allinger) Wiley Interscience, New York, 2, 199 (1967).Google Scholar

Copyright information

© Friedr. Vieweg & Sohn Verlagsgesellschaft mbH 1983

Authors and Affiliations

  • M. W. Coleman
    • 1
  1. 1.Analytical Chemistry Department, Pfizer Central ResearchPfizer LimitedSandwichUK

Personalised recommendations