The synthesis of pseudopeptides with a chiral alpha -sulfonimidoylcarboxy m
oiety in the backbone is described. Starting from readily available (S-S)-S
-methyl S-phenyl sulfoximine and various cyclic and acyclic alpha -amino ac
ids the desired products are obtained in good yields with peptide coupling
methodology, Specific secondary structures caused by intramolecular hydroge
n bends may be adopted. Results of NMR studies to reveal conformational pre
ferences will be discussed.