Enantiopure Cα-tetrasubstituted α-amino acids. Chemo-enzymatic synthesis and application to turn-forming peptides

Abstract By a chemo-enzymatic approach we carried out a large-scale synthesis of four enantiopure, sterically constrained, C α -tetrasubstituted α-amino acids, all characterized by a sidechain C γ C δ double bond. By using one of them ( l -Mag), we prepared an N α -protected tetrapeptide benzylamide which was shown to adopt a β-turn conformation and to efficiently undergo ring-closing olefin metathesis.

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