Fluoroolefin peptide isosteres - tools for controlling peptide conformations

Abstract

Fluoroolefin dipeptide isosteres were synthesized applying the Peterson reaction as a novel method for fluoroolefination. The dipeptide isosteres were elaborated to provide the conformationally constrained analogs (1-(R), 1-(S) and 2-(R), 2-(S)) of the Suc-Ala-Gly-Pro-Phe-pNA tetrapeptide, a synthetic substate of cyclophilin.