The development of synthetic helical structures undergoing stimuli-responsive chirality transformations is important for an understanding of the role of chirality in natural systems.However,controlling supramolecular chirality in entropically driven assemblies in aqueous media is challenging.T odevelop stimuli-responsive assemblies,wedesigned and synthesized pyrazine derivatives with l-alanine groups as chiral building blocks.These systems undergo self-assembly in aqueous media to generate helical fibers and the embedded alanine groups transfer their chirality to the assembled structures.F urthermore,t hese helical fibers undergo aN i 2+induced chirality transformation. The study demonstrates the role of intermolecular hydrogen bonding, p-p stacking,a nd the hydrophobic effect in the Ni 2+ -mediated transition of helical fibers to supercoiled helical ensembles which mimic the formation of superstructures in biopolymers. Figure 13. a) TEM image of the 1:Ni 2+ :d-histidines uperhelix in aqueous media. b) TEM image showing alamellar morphology.