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Synthetic Peptides: Design, Structure and Biological Function.

The synthesis of a series of polyfunctional Ca,Ca-disubstituted glycines is described. The lysine-like amino acid analog, Api, was prepared by regioselective hydrolysis of a triBoced hydantoin intermediate, followed by N“-protection to yield the first orthogonally protected ionizable Ca,Ca-disubstituted amino acid which is alicyclic in nature. The synthesis of three orthogonally protected tetrafimctional amino acids, Bap, Bglu, and Basp was envisioned by the mild alkylation of the common organic synthon ethyl nitroacetate. Subsequent regioselective modification should allow for the isolation of the first synthesized tetrafimctional amino acid derivatives suitable for solid-phase synthesis. These amino acids are designed to induce peptide secondary structure by salt-bridge stabilization. A series of peptides, incorporating 80% Ca,Ca-disubstituted glycines were synthesized to establish the helix stabilizing effect of amphipathicity in short helices. The peptides were prepared as the following permutation isomer pairs, Pi-10 & Ipi-10; Ach-lOa & Ach-10; and Cyh-10 & Ich-10. The peptides within each pair contains the same amino acid content, but with different sequences, each designed to preferentially adopt a 3 toor a-helix. Circular dichroism studies confirm that amphipathicity is a significant factor in shifting the 3io-/a-helix equilibrium, notably so in micellar environments which mimic biological membranes. The bioactivity of the aforementioned peptides was established by minimum inhibitory concentrations (MICs) against representative Gram-positive and Gram-