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A Light-Releasable Potentially Prebiotic Nucleotide Activating Agent

Mariani, Angelica, Russell, David A., Javelle, Thomas, Sutherland, John D.
Journal of the American Chemical Society 2018 v.140 no.28 pp. 8657-8661
feedstocks, irradiation, nucleosides, oligomerization, phosphates, prebiotics
Investigations into the chemical origin of life have recently benefitted from a holistic approach in which possible atmospheric, organic, and inorganic systems chemistries are taken into consideration. In this way, we now report that a selective phosphate activating agent, namely methyl isocyanide, could plausibly have been produced from simple prebiotic feedstocks. We show that methyl isocyanide drives the conversion of nucleoside monophosphates to phosphorimidazolides under potentially prebiotic conditions and in excellent yields for the first time. Importantly, this chemistry allows for repeated reactivation cycles, a property long sought in nonenzymatic oligomerization studies. Further, as the isocyanide is released upon irradiation, the possibility of spatially and temporally controlled activation chemistry is thus raised.