The Design, Synthesis and Conformation of Some New β-Hairpin Mimetics: Novel Reagents for Drug and Vaccine Discovery

Syntheses and conformational studies are presented of some novel templates for use in the construction of β-hairpin mimetics. The templates are relatively rigid molecules that constrain the backbone conformation of an attached peptide loop into the β-region of φ/ψ-space. They include diketopiperazines incorporating substituted proline derivatives, as well as heterochiral diproline units, which can be incorporated efficiently into cyclic peptide β-hairpin mimetics by solid-phase methods. Potential applications of β-hairpin mimetics in drug and synthetic vaccine discovery are discussed.

peptide - peptidomimetic - secondary structure - antibody - epitope