3.9 Article

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

Journal

CHEMSYSTEMSCHEM
Volume 4, Issue 6, Pages -

Publisher

WILEY
DOI: 10.1002/syst.202200020

Keywords

nucleotides; origin of life; phosphorylation; prebiotic chemistry; regioselectivity

Funding

  1. Max-Planck-Society (Max-Planck-Fellow Research Group Origins of Life)
  2. Volkswagen Stiftung (Initiating Molecular Life)
  3. Deutsche Forschungsgemeinschaft DFG [364653263 -TRR 235, EXC-2094 390783311]
  4. Projekt DEAL

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Nucleotides play a vital role in organisms, but there has been no effective selective pathway for their formation. In this study, we have discovered a selective nucleotide synthesis reaction pathway under extremely mild prebiotic conditions for all major bases. This finding opens up new avenues for studying the origins of life.
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.

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