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HPLC enantioseparation of phenylalanine analogs by application of (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester as a new chiral derivatizing agent

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Summary

The indirect stereochemical resolution of the enantiomers of phenylalanine analogs was studied by high-performance liquid chromatographic methods. The resolution was performed by applying pre-column derivatization with (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester, (S)-NIFE, as a new chiral derivatizing agent. Its applicability is demonstrated by the derivatization and separation of a series of ring-and α-methyl-substituted phenylalanines and phenylalanine amides, and especially by the derivatization of sterically hindered, less reactive α-methyl-substituted phenylalanine analogs. The diastereomeric, derivatives produced were separated by reversed-phase high-performance liquid, chromatography. The conditions of both derivatization and separation were optimized. The method described offers good enantioselectivity for various chiral amino compounds derived from chemo-enzymatic processes.

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Authors and Affiliations

  1. Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér, 7 6720, Szeged, Hungary

    E. Olajos & A. Peter

  2. Eenheid Organische Chemie, Vrije Universiteit Brussel, Pleinlaan 2, 1050, Brussels, Belgium

    R. Casimir & D. Tourwe

Authors
  1. E. Olajos
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  2. A. Peter
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  3. R. Casimir
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  4. D. Tourwe
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Olajos, E., Peter, A., Casimir, R. et al. HPLC enantioseparation of phenylalanine analogs by application of (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester as a new chiral derivatizing agent. Chromatographia 54, 77–82 (2001). https://doi.org/10.1007/BF02491837

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  • DOI: https://doi.org/10.1007/BF02491837

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