Carboxylate Binding by Guanidiniocarbonylpyrroles: From Self-Assembly to Peptide Receptors

Carsten Schmuck
Institut für Organische Chemie, Universität zu Köln, Greinstrasse 4
50939 Köln, Germany



We recently found that 2-(guanidiniocarbonyl)-1H-pyrroles bind carboxylates by ion pairing in combination with multiple hydrogen bonds even in highly polar solvents (K ( 103 mol-1 in 40% water in DMSO).[i]

Based on this novel recognition motif, new supramolecular structures can be designed. Self-complementary guanidiniocarbonyl pyrrole/carboxylate zwitterions form intramolecular loops,[ii] dimers[iii] or oligomers[iv] depending on the molecular structure of the zwitterion and the experimental conditions.

Guanidiniocarbonyl pyrrole cations can also be used as receptors for the stereoselective complexation of amino acids and small peptides in aqueous solvents.[v] By incorporating such guanidiniocarbonyl pyrrole units into a combinatorial receptor library, one should be able to identify receptors for the effective complexation of biologically relevant oligopetides.


[i] C. Schmuck, Chem. Comm. 1999, 843.
[ii] C. Schmuck, J. Org. Chem. 2000, 65, 2432.
[iii] C. Schmuck, Eur. J. Org. Chem. 1999, 2397.
[iv] C. Schmuck, submitted for publication.
[v] C. Schmuck, Chem. Eur. J. 2000, 6, 709.