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

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Summary

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.

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Authors and Affiliations

  1. Analytical Chemistry Department, Pfizer Central Research, Pfizer Limited, Sandwich, Kent, UK

    M. W. Coleman

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  1. M. W. Coleman
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Coleman, M.W. Determination of the enantiomeric purity of oxfenicine by high-performance liquid chromatography. Chromatographia 17, 23–26 (1983). https://doi.org/10.1007/BF02265103

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  • DOI: https://doi.org/10.1007/BF02265103

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