A molecular communication channel consisting of a single reversible chain of hydrogen bonds in a conformationally flexible oligomer

doi:10.1016/j.chempr.2021.06.022

Chem

Volume 7, Issue 9, 9 September 2021, Pages 2460-2472

https://doi.org/10.1016/j.chempr.2021.06.022 Get rights and content

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open access

Highlights

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Simple urea oligomers organize themselves with a single coherent hydrogen-bond chain
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Reversing the polarity of the hydrogen bonding sends a message through the molecule
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Conformational messages can be transmitted by changes in pH or by anion binding
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Receipt of the conformational message is indicated by a remote fluorescent response

The bigger picture

Despite the progress made by synthetic chemistry in building the molecular structures of nature, there are still domains of molecular science where biology is immensely more sophisticated than even the most advanced artificial chemical systems. One of these is the ability to use molecular structures to encode and communicate information. Nature stores information in the hydrogen-bond polarity of the base pairs and translates it into molecular function using the polarity matching of these bonds. Here, we outline an early step toward replicating this ability in the design, synthesis, and operation of a series of synthetic molecular devices that employ a structurally simple family of oligomeric molecules that can communicate information in the form of hydrogen-bond polarity. This study marks a significant step in the design of molecular systems that manipulate information, which will form the basis of the many compartmentalization-based nanotechnologies of the future.

Summary

Communication of information through the global switching of conformation in synthetic molecules has hitherto entailed the inversion of chirality. Here, we report a class of oligomer through which information may be communicated through a global reversal of polarity. Ethylene-bridged oligoureas are constitutionally symmetrical, conformationally flexible molecules organized by a single chain of hydrogen bonds running the full length of the oligomer. NMR reveals that this hydrogen-bonded chain may undergo a coherent reversal of directionality. The directional uniformity of the hydrogen-bond chain allows it to act as a channel for the spatial communication of information on a molecular scale. A binding site at the terminus of an oligomer detects local information about changes in pH or anion concentration and transmits that information—in the form of a directionality switch in the hydrogen-bond chain—to a remote polarity-sensitive fluorophore. This propagation of polarity-encoded information provides a new mechanism for molecular communication.

Graphical abstract

Keywords

dynamic foldamer

urea

conformation

hydrogen bonding

NMR

communication

information theory

oligomer

binding

stimulus responsive

UN Sustainable Development Goals

SDG3: Good health and well-being

SDG9: Industry innovation and infrastructure

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