Nature has long inspired chemists to replicate the molecules produced by evolution. Arguably, the most important of these are the nucleic acids due to their ability to store and transfer information by the means of duplex formation using Watson-Crick base pairing. Modified DNA analogues have been prepared, in which the phosphate diester units used for synthesis, the bases used for recognition, and the sugar backbones have been replaced. These systems were found to form stable duplexes, so it is clear that the precise structure of these three modules is not crucial for information manipulation through a sequence-selective duplex formation.<br/><br/>Herein, we present a new family of oligomers that contain a sequence of hydrogen-bonding recognition sites. The design uses single-point hydrogen bond recognition motifs, which provide strong interactions in non-polar organic solvents, and ester groups for the coupling chemistry required for oligomer synthesis. The poster will discuss synthetic efforts towards these new information molecules and studies of duplex formation.

Ester-based synthetic information molecules

253rd National Meeting (2017)

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