Cyclic peptides of sarcosine. Syntheses and conformation

A series of cyclic peptides of sarcosine with the general formula c-Sar-n, n=2-8, has been synthesized and conformational studies carried out both in solution and in the solid. The rings are conformationally very homogeneous and contain both cis and trans amide bonds. Their barriers to ring inversion are high; in the smaller rings this is attributed to steric hindrance, caused by the N-methyl-groups, whilst in the larger rings the folding of the chain in helical segments plays an important role.