Add time:07/27/2019         Source:sciencedirect.com

The synthesis of westiellamide (cas 131998-54-4) analogues, wherein the oxazoline units are replaced by oxazole or thiazole units, is presented. The structures of these analogues, and also of an imidazole-based analogue, were investigated using X-ray diffraction and DFT-based molecular modelling calculations. We could show that the oxazole-based peptide is almost planar, whereas the thiazole and the imidazole cyclic peptides have cone-like structures. Furthermore we could show that the flexibility of the systems essentially depends on the type of the azole building block. If oxazole-containing cyclopeptides are used, the scaffold takes an almost planar structure; bending the scaffold towards a cone-like structure, however, requires high energy. Imidazole-containing cyclopeptides show a complementary behaviour: while a planar structure can only be obtained with a high energetic input, a strong bending of the system is energetically favoured.

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