Peptides guanidiniocarbonyl pyrrole

We will demonstrate in this chapter our approach towards modular receptors for complexation of biologically relevant peptides in water. A new binding motif for carboxylates, the guanidiniocarbonyl pyrroles, has been designed this enables the formation of stable ion pairs even in aqueous solvents. By a stepwise elongation of this binding motif with additional interaction sites receptors are obtained that bind not only carboxylates but also single amino acids, both side-chain- and ste-reoselectively, and even tetrapeptides. 

R 43 C. Schmuck and L. Geiger, Carboxylate Binding by Guanidiniocarbonyl Pyrroles From Self-Assembly to Peptide Receptors , p. 1485 R 44 X. Cai and C. Dass, Conformational Analysis of Proteins and Peptides , p. 1841 Vol. 8, 2004... 

Alternatively, optimization of peptide affinity and selectivity of guanidiniocarbonyl pyrrole-derived peptide receptors has been achieved by using combinatorial methods." In this context, a library of hosts of the general structure 41 (Scheme 20) was prepared on solid support, and binding affinity was screened toward the N-protected tetrapep-tide Ac-Val-Val-Ile-Ala-0 , the C-terminal sequence of the amyloid-)S-peptide. The first investigation involved a library... 

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