Straightforward asymmetric synthesis of Ala-Ψ[CFCH]-Pro, a proline-containing pseudodipeptide bearing a fluoroolefin as a peptide bond mimic

Abstract

From ethyl-2-oxocyclopentanecarboxylate, we developed an asymmetric synthesis of the fluorinated dipeptide Ala-Ψ[(Z)CFCH]-Pro analogue of the transoid parent dipeptide. The fluorinated pseudodipeptide could be incorporated into various peptides or proteins for conformational, structural studies and biological activity studies and could also play a relevant role as an enzyme inhibitor.