Xuehong Luo

Synthesis and folding preferences of γ-amino acid oligopeptides: stereochemical control in the formation of a reverse turn and a helix

Abstract The stereoselective synthesis of α-cinnamyl γ-amino acids and the corresponding oligopeptides is described. Detailed 1D and 2D NMR studies in pyridine-d 5 show that the ( αR )-cinnamyl γ-amino acid tetrapeptide adopts a reverse turn structure, while the ( αS )-cinnamyl γ-amino acid tetrapeptide adopts a right-handed helical structure.

1,2-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful, enantiopure aspartates and constrained scaffolds

Dianions derived from N-Cbz aspartic acid esters undergo highly stereoselective anti allylation reactions at the unsubstituted carbon. The roles of additives, of the cation and of the electrophile were studied. Synthetic applications and potential utility in peptidomimetic design are also described.