Synthesis and Properties of New Fluorinated Peptidomimetics

Stereocontrolled protocols, both in solution and in solid-phase, for the synthesis of many different fluoroalkyl peptidomimetics are surveyed in this paper: (a) Tfm-malic peptidomimetics as micromolar inhibitors of some matrix metalloproteinases; (b) partially modified retro (PMR) and retro-inverso (PMRI)- ψ[CH(CF 3 )NH]-peptides with a strong proclivity to assume turn-like conformations; (c) ψ[CH(CF 3 )NH]-peptide mimics holding a great potential as hybrids between natural peptides and hydrolytic transition state analogs; (d) the first PMR-peptides incorporating a trifluoroalanine surrogate.