Functionalized Bis-Peptides.

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Summary We have now discovered a synthetic methodology for the assembly of bis-peptides that makes possible for the first time the controlled placement of functional groups of different types along the length of a bis-peptide molecule. These functional groups can be pendant to the bis-peptide chain, which can be dimeric, oligomeric or polymeric in character. Pre-organized, functionalized bis-peptides can be designed using relatively simple molecular modeling which have three-dimensional structures that are immune to denaturation, thus potentially providing significant advantages over proteins, DNA, RNA and unnatural foldamers. The control of functional group presentation can be determined by the structure of the bis-amino acids used to prepare the bis-peptides. The three-dimensional structure of the bis-peptide backbone and thus the relative orientation of the side-chains (the functional groups) can be varied as desired by controlling the stereochemistry and the sequence of the monomers utilized in constructing the bis-peptide. The constellations of functional groups in the bis-peptide can mimic active sites of proteins and protein binding surfaces.