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The Pro‐Gly motif is often involved in protein‐protein interactions and may participate in intracellular signalling cascades. Conformationally constrained short protein‐derived turn peptides thus offer promise for the development of drug candidates that could interfere with these interactions. Byrne et al . report ECD and NMR spectroscopy studies, as well as molecular dynamics simulations, that show the short 363–367 peptide motif of the human oestrogen receptor α (RVPGF) adopts a type II β‐turn around the trans Pro‐Gly motif. When the proline is substituted by a 5,5‐dimethylproline, a cis isomer adopting a type VIb β‐turn centred on the Val‐Pro segment is detected. (doi: 10.1002/pep2.24113 )