Nikmal, Arif; (2018) Studies Towards a Chemical Origins of RNA: Divergent Prebiotic Synthesis of Pyrimidine and 8-oxo-Purines Ribonucleotides. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

Elucidating a prebiotic plausible nucleotide synthesis is considered one of the greatest challenges in the origins of life research. Although separate synthesis that account for the pyrimidine and purine ribonucleotides have been developed, no divergent synthesis from a single precursor has yet been developed that accounts for the synthesis of both pyrimidine and purine ribonucleotides. Furthermore, the reported prebiotic synthesis of pyrimidine and purine nucleotides are not mutually compatible and could not co-operate under similar conditions. This thesis proposes a divergent synthesis of both anhydro-pyrimidine and anhydro-purine ribonucleotides on a regiospecific sugar scaffold, followed by concurrent phosphorylation and chemical inversion to yield pyrimidines (3 and 4) and 8-oxo-purines (93 and 187) in the natural β-ribo-stereochemistry. This concomitant approach employs only feedstock small molecules that are consider to be prebiotically plausible and condition that are consider to be reasonable under early Earth geothermal conditions. Moreover, given that 8-oxo purines and pyrimidines ribonucleotides share a common prebiotic synthetic route, it is hypothesised that 8-oxo purines could have predated natural purines in biology and that they could have played an important role in the transition of chemistry to biology and facilitated the modern Watson-Crick base pairing system.

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