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A new strategy to induce gamma-turns: peptides composed of alternating alpha-aminoxy acids and alpha-amino acids.

It is known that the seven-membered-ring intramolecular hydrogen bond (gamma-turn) is seldom formed in naturally occurring peptides composed of alpha-amino acids. Here we report a new strategy to induce gamma-turns in short linear peptides. We designed and synthesized several peptides (1-5) containing alternating alpha-l-aminoxy acids and alpha-d-amino acids. 1H NMR studies revealed that the gamma-turn could be initiated by the following N-O turn, an eight-membered-ring intramolecular hydrogen bond induced by an alpha-aminoxy acid. Moreover, NOESY and CD studies suggested peptides 4 and 5 form a novel secondary structure, a mixed 7-8 helix. Theoretical calculations on several di-, tri-, and tetrapeptide models provided strong support to the above conclusions.