Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemist's 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.

Automated summary

In order to fine-tune the effects of proline on bioactive compounds, various modifications have been made to its structure over the years. Notably, the introduction of a cyclopropane ring or a fluorine atom has shown interesting results. In this study, a proline containing fluorocyclopropane was synthesized and inserted into a tripeptide, and its conformation was analyzed using nuclear magnetic resonance and density functional theory calculations.