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Activated carbamate reagent as chiral derivatizing agent for liquid chromatographic optical resolution of enantiomeric amino compounds

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Summary

A chiral derivatization reagent having activated succinimido carbamate moieties were developed for the optical resolution of enantiomeric amines by high-performance liquid chromatography. Succinimido R-(+)- or S-(−)-1-phenylethyl and R-(+)- or S-(−)-1-(α-naphthyl)-ethyl carbamates were synthesized by the reaction of optically active phenylethyl and naphthylethyl amines with discuccinimido carbonate (DSC). These reagents reacted with both primary and secondary amine enantiomers such as amino acids and β-amino alcohols to give the corresponding diastereomeric urea derivatives. These diastereomers were efficiently separated by reversed-phase liquid chromatography and detected by their absorption or the fluorescence of the chromophores. The chiral derivatization procedure was applied to the separation and determination of enantiomeric propranolol in serum.

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Authors and Affiliations

  1. Laboratory of Analytical Chemistry, School of Pharmaceutical Sciences, Kitasato University, 9-1 Shirokane-5, 108, Minato-ku, Tokyo, Japan

    K. Iwaki, S. Yoshida, N. Nimura & T. Kinoshita

  2. Laboratory of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Kitasato University, 9-1 Shirokane-5, 108, Minato-ku, Tokyo, Japan

    K. Takeda & H. Ogura

Authors
  1. K. Iwaki
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  2. S. Yoshida
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  3. N. Nimura
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  4. T. Kinoshita
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  5. K. Takeda
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  6. H. Ogura
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Iwaki, K., Yoshida, S., Nimura, N. et al. Activated carbamate reagent as chiral derivatizing agent for liquid chromatographic optical resolution of enantiomeric amino compounds. Chromatographia 23, 899–902 (1987). https://doi.org/10.1007/BF02261468

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  • DOI: https://doi.org/10.1007/BF02261468

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