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

Abstract

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 into another. The process is useful to synthesise structures and thus functions that might be difficult to create otherwise and reaches exquisite levels of efficiency in biological systems as illustrated by protein expression from mRNA templates1,2 or by the assembly of the tobacco mosaic virus capsid protein according to the length of its RNA3. In synthetic systems, examples of template-directed syntheses are numerous4–6, 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 optimised7–10. Here we show high-fidelity enzyme-free translation of long rod-like alkylcarbamate oligomers into well-defined sequences of stacked helical aromatic oligoamides. Features present in the rods, including the number and distance between carbamate functions and stereogenic centres, template the self-assembly of complementary stacks of helices each having 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 (foldamers11) that may, for example, serve as scaffolds to organize appended functional features at positions in space defined with atomic precision across nanometric distances.