NOVEL FOLDING PATTERNS IN A FAMILY OF OLIGOANTHRANILAMIDES - NONPEPTIDE OLIGOMERS THAT FORM EXTENDED HELICAL SECONDARY STRUCTURES

Anthranilamide derivatives are used as the basis for a series of novel oligomers that fold into helical secondary structures in the solid st ate. When combined with pyridine-2,6-dicarboxylic acid and 4,6-dimetho xy-1,3-diaminobenzene subunits, oligoanthranilamides can be induced to take up a coiled conformation corresponding to two turns of a helix. X-ray crystallography shows that intramolecular hydrogen bonding and p i-pi stacking interactions are important in stabilizing the extended h elical structures. Furthermore, both experimental and calculated H-1 N MR methods indicate that related conformations are taken up by the oli gomers in chloroform solution.