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Expedient Synthesis of Fmoc-(S)-γ-Fluoroleucine and Late-Stage Fluorination of Peptides
Journal article   Peer reviewed

Expedient Synthesis of Fmoc-(S)-γ-Fluoroleucine and Late-Stage Fluorination of Peptides

Roberto Fanelli, Jean Martinez and Florine Cavelier
SYNLETT, Vol.27(09), pp.1403-1407
17/05/2016

Abstract

(S)-γ-fluoroleucine peptides stereoselective synthesis Selectfluor late-stage fluorination
A concise synthesis of (S)-γ-fluoroleucine is described in five steps from commercially available compounds, with an overall yield of 57%. The Markovnikov hydrofluorination reaction of the unsaturated amino acid precursor as last step of the synthesis proved to be effective. This fluorination can also be performed directly on a short peptide model with the same efficiency. This reaction could be in principle applicable for the preparation of radiolabeled amino acids and peptides.
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