Proline (Pro) is the only common amino acid in proteins that does not undergo phosphorylation. Phosphorylation occurs on hydroxyl-containing amino acids: serine (Ser, A), threonine (Thr, B), and tyrosine (Tyr, D). These hydroxyl groups serve as nucleophilic targets for kinases. Proline has a secondary amine as its side chain (it's an imino acid that forms a cyclic structure with the backbone), lacking any hydroxyl group that could be phosphorylated. This unique structure also makes proline a helix breaker in protein secondary structure.