POS1-0659
Encoding nucleobase sequences to synthetic polyesters using adenine/thymine-containing isocyanides as gluing components for the Passerini IEG
When and Where
Nov 30, -0001
12:00am - 12:00am
Presenter(s)
Hyojoo Noh (Seoul National University)
Co-Author(s)
Abstract
DNA exhibits programmable self-assembly through complementary hydrogen bonding between nucleobases introduced to sugar phosphate backbones in defined sequences, inspiring the development of synthetic analogs with nucleobases as recognition motifs. However, most nucleobase-containing polymers lack defined monomer sequences or molecular uniformity, limiting their biomimetic precision. In this work, we synthesized sequence-defined polymers bearing adenine and thymine units via the Passerini iterative exponential growth strategy. Butoxycarbonyl (Boc)-protected nucleobase-functionalized isocyanides were employed to construct poly(hydroxybutyrate) bearing butyl- and Boc-thymine side chains and poly(hydroxybutyrate) with butyl- and Boc-adenine side chains with uniform molecular weights. After Boc deprotection, NMR analyses revealed complementary adenine–thymine hydrogen bonding, showing characteristic downfield shifts in a 1:1 mixture, an association constant of 320 M−¹ obtained by NMR titration, and thermoreversible behavior in variable-temperature NMR experiments. Furthermore, adenine and thymine were incorporated into a single polymer backbone, demonstrating the method’s ability to encode programmable hydrogen-bonding motifs into uniform synthetic macromolecules.
