Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemistʼs Toolbox

Over the years, numerous
modifications to the structure of proline
have been made in order to tune its effects on bioactive compounds.
Notably, the introduction of a cyclopropane ring or a fluorine atom
has produced interesting results. Herein, we describe the synthesis
of a proline containing fluorocyclopropane. This modified amino acid
was inserted into a tripeptide, whose conformation was studied by
nuclear magnetic resonance and density functional theory calculations.