Synthesis and use of N-Fmoc-l-fluoroalanine

• DOI: 10.1016/j.tetlet.2015.01.117
• Publication Date: 2015-01-30T08:03:33Z
• Authors: Claudia Carpentier; Raphaël Godbout; François Otis; Normand Voyer
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract We report a practical synthesis of N -Fmoc protected l -fluoroalanine 6 from l -serine. The key step involves a deoxofluorination reaction which was best achieved using XtalFluor-E in the presence of triethylamine trihydrofluoride. We also report the use of 6 in solid-phase peptide synthesis for the preparation of a model tripeptide demonstrating the possibility of incorporating a fluorinated probe in a peptide without elimination. Furthermore, cleavage of the dipeptide permitted to verify that 6 has a high enantiopurity.