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Peptoid–Peptide Hybrid Ligands Targeting the Polo Box Domain of Polo‐Like Kinase 1

We replaced the amino terminal Pro residue of the Plk1 polo‐box‐domain‐binding pentapeptide (PLHSpT) with a library of N‐alkyl‐Gly “peptoids”, and identified long‐chain tethered phenyl moieties giving greater than two‐orders‐of‐magnitude affinity enhancement. Further simplification by replacing the peptoid residue with appropriate amides gave low‐nanomolar affinity N‐acylated tetrapeptides. Binding of the N‐terminal long‐chain phenyl extension was demonstrated by X‐ray co‐crystal data.