Quinolines are an established class of aromatic pharmacophores replete in natural products, FDA-approved drugs, and high-affinity ligands for both protein and RNA. Quinoline-containing small molecules that engage proteins include FDA-approved therapeutics such as chloroquine, moxifloxacin, topotecan, lenvatinib, and saquinavir, which is itself a peptidomimetic with an N-terminal quinoline . Quinolines are especially privileged with respect to RNA : Quinoline-peptide conjugates function as helix-threading intercalators , and substituted quinolines are found within small molecules that target pre-mRNA to modulate splicing . Perhaps the most unique aspect of the quinoline pharmacophore is its ability to support axial chirality and exist, in certain cases, as stable atropisomers. This stereochemical complexity would add a new level of topological diversity to genetically encoded linear or cyclic peptides.