RNA-inspired intramolecular transesterification accelerates the hydrolysis of polyethylene-like polyphosphoesters

Tobias P. Haider, Oksana Suraeva, Ingo Lieberwirth, Piotr Paneth, Frederik R. Wurm*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
23 Downloads (Pure)


To synthesize new (bio)degradable alternatives to commodity polymers, adapting natural motives can be a promising approach. We present the synthesis and characterization of degradable polyethylene (PE)-like polyphosphoesters, which exhibit increased degradation rates due to an intra-molecular transesterification similar to RNA. An α,ω-diene monomer was synthesized in three steps starting from readily available compounds. By acyclic diene metathesis (ADMET) polymerization, PE-like polymers with molecular weights up to 38 400 g mol−1were obtained. Post-polymerization functionalization gave fully saturated and semicrystalline polymers with a precise spacing of 20 CH2groups between each phosphate group carrying an ethoxy hydroxyl side chain. This side chain was capable of intramolecular transesterification with the main-chain similar to RNA-hydrolysis, mimicking the 2′-OH group of ribose. Thermal properties were characterized by differential scanning calorimetry (DSC (Tmca.85 °C)) and the crystal structure was investigated by wide-angle X-ray scattering (WAXS). Polymer films immersed in aqueous solutions at different pH values proved an accelerated degradation compared to structurally similar polyphosphoesters without pendant ethoxy hydroxyl groups. Polymer degradation proceeded also in artificial seawater (pH = 8), while the polymer was stable at physiological pH of 7.4. The degradation mechanism followed the intra-molecular “RNA-inspired” transesterification which was detected by NMR spectroscopy as well as by monitoring the hydrolysis of a polymer blend of a polyphosphoester without pendant OH-group and the RNA-inspired polymer, proving selective hydrolysis of the latter. This mechanism has been further supported by the DFT calculations. The “RNA-inspired” degradation of polymers could play an important part in accelerating the hydrolysis of polymers and plastics in natural environments,e.g.seawater.

Original languageEnglish
Pages (from-to)16054-16064
Number of pages11
JournalChemical science
Issue number48
Early online date23 Nov 2021
Publication statusPublished - 28 Dec 2021


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