Fluorinated Cyclopropane Amino Acids: from Synthesis to structural Implication in peptides for biological Applications – FLUORAAC

The FLUORAAC project aims to develop original accesses to cyclopropane amino acids bearing fluorinated groups (CF3, CF2H and CH2F) or a fluorine atom from nitro diazo acetates and alkenes bearing a fluorinated group. Other methodologies from diazo compounds bearing a CF3 or CF2H group and from an alkene with a masked amino acid function will also be studied. For this, new rhodium catalysts will be developed using theoretical calculation approaches and will also call on artificial intelligence. These chiral cyclopropane motifs bearing a fluorinated group will then be incorporated on the one hand into model peptide structures to understand the consequences of the introduction of such a motif into the three-dimensional structure of the peptide. For this, several analytical techniques such as nuclear magnetic resonance or infrared spectroscopy will be used. Finally, these motifs will also be integrated into the minimal structure of neurotensin and cathepsin D in order to study the biological activities of these cyclopropane analogues.