Translation of rod-like template sequences into homochiral assemblies of stacked helical oligomers

At the molecular level, translation refers to the production of a new entity according to a template that has a different chemical composition. In this way, chemical information may be translated from one molecule to another. The process is useful to synthesize structures and thus functions that might be difficult to create otherwise, and it reaches exquisite levels of efficiency in biological systems, as illustrated by protein expression from mRNA templates(1,2) or by the assembly of the tobacco mosaic virus capsid protein according to the length of its RNA(3). In synthetic systems, examples of template-directed syntheses are numerous(4-6), but general and versatile schemes in which a non-natural sequence actually encodes the information necessary to produce a different sequence are few and far from being optimized(7-10). Here we show a high-fidelity enzyme-free translation of long rod-like alkylcarbamate oligomers into well-defined sequences of stacked helical aromatic oligoamides. The features present in the rods, which include the number and distance between carbamate functions and stereogenic centres, template the self-assembly of complementary stacks of helices that each have a defined right (P) or left (M) handedness, length and single or double helicity. This process enables the production of very large (>20 kDa) abiotic artificial folded architectures (foldamers(11)) that may, for example, serve as scaffolds to organize appended functional features at positions in space defined with atomic precision across nanometric distances.