Organic Chemistry

Non-natural, but highly functionalized amino acids are of strongly growing interest in drug discovery and biology, especially when they restrict the conformational mobility of peptides, proteins or enzymes. With this project new cyclic β-amino acids with additional donor functions will be synthesized stereoselectively in only a few steps by using a tandem process consisting in conjugate addition of allylic alkoxides to chiral nitroalkenes and Cu-mediated radical cyclizations as the keystep and functional group modifications. The resulting tetrahydrofuran amino acids will be used to construct oligopeptides (foldamers) via peptide coupling, whose conformation and biological properties will be investigated.