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Synthesis, resolution, and determination of absolute configuration of protected α-ethynylphenylalanine enantiomers

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Abstract

Racemic-protected α-ethynylphenylalanine was synthesized from dl-2-benzylserine using α-benzylserinal as key intermediate and was successfully resolved by HPLC on a chiral stationary phase at a semipreparative scale. The absolute configuration of both enantiomers was determined by vibrational circular dichroism.

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Acknowledgments

We gratefully thank the French “ministère de l’éducation nationale, de l’enseignement supérieur et de la recherche” for its financial support. We thank graduate students for their help in the synthesis: Magali Blum, Clément Bonnel.

Conflict of interest

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. UNIV. NIMES, EA7352 CHROME, Rue du Dr G. Salan, 30021, Nîmes Cedex 1, France

    Z. Benfodda, D. Bénimélis & P. Meffre

  2. IBMM, UMR-CNRS5247, Universités Montpellier 1 and 2, Place Eugène Bataillon, 34095, Montpellier, France

    Z. Benfodda, D. Bénimélis, V. Rolland & P. Meffre

  3. Aix Marseille Université, Centrale Marseille, CNRS, ISm2 UMR 7313, 13397, Marseille, France

    M. Jean

  4. Spectropole, Aix Marseille Université, 13397, Marseille Cedex 20, France

    J.-V. Naubron

Authors
  1. Z. Benfodda
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  2. D. Bénimélis
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  3. M. Jean
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  4. J.-V. Naubron
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  5. V. Rolland
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  6. P. Meffre
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Corresponding author

Correspondence to Z. Benfodda.

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Handling Editor: J. Leban.

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Benfodda, Z., Bénimélis, D., Jean, M. et al. Synthesis, resolution, and determination of absolute configuration of protected α-ethynylphenylalanine enantiomers. Amino Acids 47, 899–907 (2015). https://doi.org/10.1007/s00726-015-1917-1

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  • DOI: https://doi.org/10.1007/s00726-015-1917-1

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