Amino Acids

, Volume 47, Issue 5, pp 899–907 | Cite as

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

  • Z. BenfoddaEmail author
  • D. Bénimélis
  • M. Jean
  • J.-V. Naubron
  • V. Rolland
  • P. Meffre
Original Article


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.


α-Ethynylphenylalanine Quaternary amino acids Unsaturated amino acid Chiral HPLC resolution Absolute configuration 



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.

Supplementary material

726_2015_1917_MOESM1_ESM.pdf (517 kb)
Supplementary material 1 (PDF 517 kb)


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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Z. Benfodda
    • 1
    • 2
    Email author
  • D. Bénimélis
    • 1
    • 2
  • M. Jean
    • 3
  • J.-V. Naubron
    • 4
  • V. Rolland
    • 2
  • P. Meffre
    • 1
    • 2
  1. 1.UNIV. NIMESNîmes Cedex 1France
  2. 2.IBMM, UMR-CNRS5247, Universités Montpellier 1 and 2MontpellierFrance
  3. 3.Aix Marseille Université, Centrale Marseille, CNRS, ISm2 UMR 7313MarseilleFrance
  4. 4.Spectropole, Aix Marseille UniversitéMarseille Cedex 20France

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