Organic Synthesis

Organic Synthesis
Engineering- Quota 165
Research Activity
Research Activity
Organic chemistry and Chemical biology with non natural molecules
The main interest of the research group is directed towards the synthesis of small, polyfunctionalized organic molecules, in particular β-amino acids and nitrogen containing heterocycles, in order to obtain novel compounds with definite biological activity. In particular, we envisaged the synthesis of peptidomimetics containing analogues of natural amino acids, in order to identify new bioactive structures leading selectively to cytotoxic drugs, enzyme inhibitors or diagnostic tools for identification of tumor cells. The biological activity of the synthesized products is evaluated in collaboration with research groups having a recognized expertise in their specific fields. In addition, for some years we were engaged in the synthesis of organic compounds of medium size (500 to 3000 amu approximately) pseudopeptidic structure, where natural amino acids are completely or partially replaced by synthetic structures chosen to impose a local conformational restriction which favors the formation of ordered secondary structure. These compounds, which are defined foldamers, can have many applications, both as pharmacologically active compounds (for an example, they are able to inhibit protein-protein interactions) and as new supramolecular materials with interesting properties. Our group currently synthesizes, purifies and analyzes these compounds, which are useful for a lot of applications in chemical biology. At present we are developing new monomers and oligomers containing conformational constraints sterically ordered that form helices of various sizes. (click on images to enlarge)

foldamero a elica-8


  Research Projects
1. Synthesis of amphiphilic foldamers displaying a helix-8 structure. These products are obtained starting from substituted hydrazido acids, in order to obtain products with antibiotic activity, to be tested against different bacterial species. 
2. Preparation of new units for build-up of foldamers. These molecules arise from the parent γ-lactam structure, by insertion of heteroatoms, in order to change the H-bond system and then the foldamer conformation in solution. 
3. Synthesis of foldamers displaying a retro-inverso structure, directed towards preparation of amphiphilic molecules with antibiotic activity, where the amide bonds are not recognized by proteases. 
4. Synthesis of foldamers bearing 1,2,3-triazol rings, introduced via “click chemistry”, which are able to complex tubulins.
5. Use of “click-chemistry” having as targets guanines bonded each other with linkers having different lenghth and functionalization, directed towards build-up of ordered structures and supramolecular systems. 
6. Synthesis of functionalized foldamers, aimed to preparation of novel difunctional catalysts, to be used either in homogeneous or in solid phase. 
tel. 071 2204720
tel. 071 2204233
Dott. Annafelicia Civitavecchia
Dott. Paolo Amabili
HPLC HP 1100

Beckmann OLIGO 1000

(NMR 400 MHz) Polarimetro Polax D