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Claudia Tomasini

Full Professor

Department of Chemistry "Giacomo Ciamician"

Academic discipline: CHIM/06 Organic Chemistry


Keywords: conformational analysis supramolecular materials biomaterials foldamers peptides peptidomimetics

• Synthesis of new pseudopeptides for the formation of secondary structures.
• Analysis of the behaviour of small oligomers in solution and in the solid state for the formation of supramolecular materials.
• Synthesis andapplication of new catalysts for the organocatalysis.

We synthesize and study the properties of synthetic molecules that belong to the family of peptidomimetics. Recently, the research field of peptides has included peptidomimetics that are synthetic compounds able to mimic the shape and the function of natural peptides, although they contain different functional groups and/or have a different chemical structure. These compounds are also called "foldamers", as they are able to self-organize, thus forming secondary structures, such as helixes or sheets. These molecules can be tested as new drugs, as they are unchanged in living cells for longer times than natural peptides.

We are studying the synthesis and the properties of hetero-oligomers containing natural or synthetic amino acids: they can be linear or cyclic, thus mimicking secondary structures, such as helixes, turns or sheets. These compounds can act also as molecular receptors of metal cation, such as calcium or magnesium. More recently we have observed that some classes of oligomers tend to assume an ordered structure in the solid state, thus forming fibres and fibrils that can be observed with the microscope. Aggregation and disaggregation are central phenomena in nature, and the self-organization of proteins is very important because fibrous proteins are involved in both intra- and extra-cellular functions. For instance, several illnesses, such as Alzheimer disease or diabetes are induced by beta-amyloid peptides that are a class of natural peptides that tend to aggregate in the blood. Our pseudopeptides have been designed with the aim of interfering with this process.

Finally our pseudopeptides can be used as catalysts for environmentally friendly reactions, thus mimicking aldolase enzymes. Indeed it has been demonstrated that proline can be utilized as a non-toxic and cheap catalyst in reaction that proceed through the formation of enamine intermediate. Following this approach, we prepared enantiomerically pure compounds with anticancer activity.

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