Many successful applications of foldamers exploit their ability to mimic, in a relatively static way, the shape of biomolecules in recognition events. Recently a dynamic aspect was added to foldamer chemistry, showing that conformationally flexible amide foldamers can behave as synthetic analogues of proteins involved in signal transduction. Interaction of ligands with a binding site induces conformational changes that propagate through the foldamer, communicating information down the chain to a remote site, reminiscent of the way that membrane-bound receptors such as GPCRs carry messages across cell membranes by conformational switching alone.<br/>The presentation will describe our efforts to develop urea-functionalized polyamines that form continuous hydrogen-bond networks with reversible polarity. The ureas are conformationally mobile, with the possibility of orientating their hydrogen-bond accepting carbonyl group towards either end of the foldamer chain. We show that it is possible to orientate the whole network by inducing one end of the chain to switch in function from a hydrogen bond acceptor to a hydrogen bond donor.

Dynamic communication through reorganizable hydrogen bond networks

255th National Meeting (2018)

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