Selective Phosphorylation of RNA- and DNA-Nucleosides under Prebiotically Plausible Conditions

Abstract

Nucleotides play a fundamental role in organisms, from adenosine triphosphate (ATP), the body‘s main source of energy, to cofactors of enzymatic reactions (e. g. coenzyme A), to nucleoside monophosphates as essential building blocks of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). Although nucleotides play such an elemental role, there is no pathway to date for the selective formation of nucleoside 5′-monophosphates. Here, we demonstrate a selective reaction pathway for 5’ mono-phosphorylation for all canonical purine and pyrimidine bases under exceptionally mild prebiotic relevant conditions in water and without using a condensing agent. The pivotal reaction step involves activated imidazolidine-4-thione phosphates. The selective formation of non-cyclic mono-phosphorylated nucleosides represents a novel and unique route to nucleotides and opens exciting perspectives in the study of the origins of life.