Effect of proline analogues on the conformation of elastin peptides

Abstract

Three elastin model peptides containing the repetitive motif –VGVXGVG–, where X corresponds to (2S)-proline (Pro), (2S,4R)-4-hydroxy-proline (Hyp) and (2S,4R)-4-methoxy-proline (Mop), were synthesized in order to define the effect of the introduction of an electronegative group on the conformation and self-assembling properties of the peptides. Circular dichroism, NMR and FT-IR spectroscopies evidenced outstanding differences at molecular and supramolecular level. This work constitutes the basis for the proper design of elastin-inspired drugs with tailored conformational properties.