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Chiral groups attached to the end of quinoline-derived oligoamide foldamers give rise to chiral helical induction in solution. The right-handed or left-handed helical sense favored by the terminal chiral group could be determined unambiguously using X-ray crystallography.

A new strategy is proposed to control the relative orientation of two folded helical oligomers in such a way that they diverge from an aromatic linker and have opposite helical handedness. The concept is validated using the helical conformations of oligoamides of 8-amino-2-quinolinecarboxylic acids.

Short peptides are induced into [alpha]-helix conformations in water through enclathration to an artificial hydrophobic cavity. Peptides with two aromatic residues have displayed high affinity for the host and these intermolecular aromatic-aromatic interactions have driven the helical folding of short peptides.

The discovery of improved and remarkably regioselective electrophilic substitutions in helically folded aromatic oligoamides is described. The reaction selectivity depends on the presence of substituents that are remote from the reaction site.

The synthesis of various 1,8-diaza-4,5-dialkoxy-2,7-anthracene dicarboxylic acid derivatives and their incorporation into cyclic and helically folded aromatic oligoamides are described. Longer, noncyclic oligoamides composed of one or two diaza-anthracene units have adopted helical conformations that have existed preferentially as double helical dimers.

A description of the design and synthesis of new amphipathic helical oligoamides based on quinoline-derived amino acids having either hydrophobic or cationic side chains is presented. Amphipathic helices are versatile targets to of investigation in view of their importance in a variety of biological processes, and the unique structure and properties of the quinoline-derived oligoamides might allow new structure-activity relationships to be developed.

The reasons for the handedness of helical polymers or oligomers that has attracted widespread interest are provided. Solution state-solid state equilibrium provides an original means to control helical handedness in synthetic oligomers.

Oligoamides of 2,6-diaminopyridine and 2,6-pyridinedicarboxylic acid (AOAS) fold into stable single helices and hybridize into double-helical dimes in solution and in the solid. Hybridization of N-oxide oligomers proceeds in a similar manner as that for the native strands extending the register of structures capable of forming double-helical dimmers and opening the way toward cross-hybridization experiments.