(+)-Fluorenylethylchloroformate (FLEC)--improved synthesis for application in chiral analysis and peptidomimetic synthesis

Org Biomol Chem. 2013 Apr 28;11(16):2571-3. doi: 10.1039/c3ob40218e.

Abstract

An efficient synthesis of the enantiomers of fluorenylethylchloroformate (FLEC) has been achieved that allows the routine application of the reagent for the resolution of chiral amines including unusual amino acids. The utility of the fluorenylethoxycarbonyl (Feoc) group as a chiral Fmoc equivalent, for combined resolution and protection of amino acids, in solid phase peptide synthesis is also shown.

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry
  • Chromatography, High Pressure Liquid
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Indicators and Reagents
  • Peptidomimetics / chemical synthesis*
  • Peptidomimetics / chemistry
  • Solid-Phase Synthesis Techniques
  • Stereoisomerism

Substances

  • Amino Acids
  • Fluorenes
  • Indicators and Reagents
  • Peptidomimetics
  • 1-(9-fluorenyl)ethyl chloroformate