Base pairing analysis of nucleobase functionalized monomers

Abstract

Nucleobases are key components in the storage of genetic information within the biopolymer called DNA. Besides their function in DNA, they have potential applications in synthetic polymer chemistry. A controlled radical polymerization technique enables the sequence-defined implementation of these nucleobases into synthetic polymers, which mimics the structure of DNA. Unfortunately, the low yield of this technique limits the length of the obtainable polymers, preventing them from being used in biomedical applications. Potential pathways towards increasing the yield rely on selective base pairing between the nucleobases, which is a phenomenon that still needs verification and characterization. The objective of this research is the characterization of hydrogen bonding between the nucleobases implemented into polymerizable monomers. Two proposed analysis techniques, based on nuclear magnetic resonance, have been used to characterize this base pairing. The analysis revealed the presence of a complex stoichiometry and the influences of temperature, solvent polarity and concentration ratios on base pairing between the monomers. Even though, this thesis revealed important effects and phenomena in base pairing, research confirming these conclusions is still required. Nevertheless, the results imply that the previously mentioned parameters could be optimized to obtain the desired selective base pairing between the nucleobase containing monomers. Therefore, the two potential pathways might indeed resolve the low yield problem.