Amino Acids

, Volume 47, Issue 5, pp 899–907

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

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

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.

Keywords

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

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
  • 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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