Bulky α, β-Dehydroamino acids (ΔAAs) can improve the proteolytic stability of peptides that contain them, presumably by altering the shape of the backbone of the peptide and by stabilizing folded states through their rigidifying effect. The stabilizing effects of ΔAAs that contain at least one hydrogen atom at the β-carbon are well-known, but the stabilizing role of bulky ΔAAs that contain fully substituted β-carbons in larger peptides is less explored. We have developed protocols for the efficient solid-phase peptide synthesis (SPPS) of simple peptides containing bulky ΔAAs, synthesized three β-Hairpin analogs and are working to explore their effects in the stability of these larger peptides. We hypothesize that bulky ΔAAs will restrict rotation of the peptide backbone and thereby stabilize secondary structures. This work may pave the way for the efficient and rapid syntheses of stabilized therapeutic agents via SPPS.

Solid-phase peptide synthesis (SPPS) of bulky α, β- dehydroamino acid-containing peptides to assess their stabilities to proteolysis

251st National Meeting (2016)

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