From Azidoproline to Functionalizable Molecular Scaffolds and Collagen Helma Wennemers Laboratorium für Organische Chemie, ETH Zürich, Wolfgang Pauli Strasse 10, CH-8093 Zürich [email protected]

Functionalizable molecular scaffolds with a well-defined conformation have become more and more important in recent years for applications ranging from the development of cell penetrating compounds, inhibitors of protein-protein interactions to new materials. We have developed azidoproline (Azp) containing oligoprolines as conformationally well-defined molecular scaffolds that allow for facile functionalization using, for example, “click chemistry”.1,2 Conformational studies demonstrated that oligoprolines containing Azp residues adopt already at chain lengths as short as six residues the well-defined polyproline II (PPII) helix. The modular synthesis allows for functionalizing the azido groups with different functional groups and even groups as large as carbohydrates and peptides can be readily introduced.2-5

The presentation will focus on the conformational properties of azidoprolines and Azpcontaining oligoprolines and their use for various applications. In addition, recent work on the development of functionalizable collagen model peptides will be discussed.6

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1. L.-S. Sonntag, S. Schweizer, C. Ochsenfeld, H. Wennemers, J. Am. Chem. Soc. 2006, 128, 14697-14703. 2. (a) M. Kümin, L.-S. Sonntag, H. Wennemers, J. Am. Chem. Soc. 2007, 129, 466-467. (b) R. S. Erdmann§, M. Kümin, H. Wennemers, Chimia 2009, 63, 197-200. 3. M. Kuemin, S. Schweizer, C. Ochsenfeld, H. Wennemers, J. Am. Chem. Soc. 2009, 131, 15474–15482. 4. M. Kuemin, J. Engel, H. Wennemers, J. Pept. Sci. 2010, 16, 596-600. 5. M. Kuemin, Y. A. Nagel, S. Schweizer, F. W. Monnard, C. Ochsenfeld, H. Wennemers, Angew. Chem. Int. Ed. 2010, 49, 6324 –6327. 6. (a) R. S. Erdmann, H. Wennemers, J. Am. Chem. Soc. 2010, 132, 13957–13959. (b) R. S. Erdmann, H. Wennemers, Angew. Chem. Int. Ed. 2011, 50, 6835-6838. (c) R. S. Erdmann, H. Wennemers, Synthesis 2009, 143-147. (d) R. S. Erdmann, H. Wennemers, Org. Biomol. Chem. 2012, in press.