(For detailed research projects visit the individual group members) Our main research interests are the design of artificial receptors for biological relevant substrates such as peptides and carbohydrates using both de-novo design and combinatorial methods, the study of self-assembling zwitterions as building blocks for supramolecular polymers in water and the thermodynamic study of non-covalent interactions in general.
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We recently found that 2-(guanidiniocarbonyl)-1H-pyrroles bind carboxylates by ion pairing in combination with multiple hydrogen bonds even in aqueous solvents (K » 103 mol-1 in 40% water in DMSO).[1] |
Based on this novel recognition motif, new supramolecular structures can be designed. Self-complementary guanidiniocarbonyl pyrrole/carboxylate zwitterions form intramolecular loops,[2] dimers[3] or oligomers[4] depending on the molecular structure of the zwitterion and the experimental conditions. These binding motifs might be useful for the design of new materials such as supramolecular polymers. Guanidiniocarbonyl pyrrole cations can also be used as receptors for the side chain selective- and stereoselective complexation of amino acids[5] and small peptides[6] in aqueous solvents. By incorporating such guanidiniocarbonyl pyrrole units into a combinatorial receptor library 1, one can also identify receptors for the effective complexation of biologically relevant oligopetides 2.[7]
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| [1] C. Schmuck, L. Geiger; Curr. Org. Chem. 2003, 7, 1485-1502. [2] C. Schmuck, J. Org. Chem. 2000, 65, 2432. [3] C. Schmuck, W. Wienand, J. Am. Chem. Soc. 2003, 125, 452-459. [4] C. Schmuck, Tetrahedron 2001, 57, 3063. [5] C. Schmuck, Chem. Eur. J. 2000, 6, 709. [6] C. Schmuck, L. Geiger, J. Am. Chem. Soc. in press. [7] C. Schmuck, M. Heil, Org. Biomol. Chem. 2003, 1, 633-636, ChemBioChem. 2003, 4, 1232-1238. |