An approach to enantiomerically pure inverse γ-turn mimetics for use in solid-phase synthesis

Article abstract of DOI:10.1016/S0040-4039(97)00692-8

An inverse γ-turn mimetic, having a morpholin-3-one ring as the key structural unit, was prepared in enantiomerically pure form in seven steps and 37% overall yield starting from 2(R)-[1'(S)-azido-2'-phenylethyl]oxirane (3). The mimetic has side-chains corresponding to a Phe-Ala-Ala tripeptide but the synthetic route was designed to allow incorporation also of other side chains. Molecular mechanics calculations revealed that the torsional angles of the second residue of the mimetic were effectively locked into an inverse γ-turn like conformation.