Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions

  title={Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions},
  author={Matthew W. Powner and B{\'e}atrice Gerland and John D. Sutherland},
At some stage in the origin of life, an informational polymer must have arisen by purely chemical means. According to one version of the ‘RNA world’ hypothesis this polymer was RNA, but attempts to provide experimental support for this have failed. In particular, although there has been some success demonstrating that ‘activated’ ribonucleotides can polymerize to form RNA, it is far from obvious how such ribonucleotides could have formed from their constituent parts (ribose and nucleobases… 
Selective prebiotic formation of RNA pyrimidine and DNA purine nucleosides
A prebiotic synthesis of the purine DNA nucleosides (deoxyadenosine and deoxyinosine) in which the pyrimidine RNA nucleoside persist has implications for the coexistence of DNA and RNA at the dawn of life.
A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization.
A long-sought route through ribose aminooxazoline to the pyrimidine β-ribonucleosides and their phosphate derivatives is described that involves an extraordinarily efficient photoanomerization of α-2-thioribocytidine.
Unified prebiotically plausible synthesis of pyrimidine and purine RNA ribonucleotides
The synthesis of the pyrimidine nucleosides from small molecules and ribose is reported, driven solely by wet-dry cycles and is compatible with purine synthesis, allowing the concurrent formation of all Watson-Crick bases.
Abiotic synthesis of purine and pyrimidine ribonucleosides in aqueous microdroplets
A general synthetic path for ribonucleosides, both purine and pyrimidine bases, is shown, using an abiotic salvage pathway in a microdroplet environment with divalent magnesium ion (Mg2+) as a catalyst.
Formation of Nucleosides and Nucleotides in Chemical Evolution
The selective formation of nucleoside with a β-ribofuranose component is described and the one-pot synthesis of nucleotides is touched on, suggesting the RNA world hypothesis has reached a deadlock.
Prebiotic stereoselective synthesis of purine and noncanonical pyrimidine nucleotide from nucleobases and phosphorylated carbohydrates
It is shown that the phosphorylated ribonucleoside building blocks for RNA can be made stereoselectively under a prebiotic plausible condition with canonical and noncanonical purines, and with one non canonical pyrimidine, and that threose nucleoside phosphates can be synthesized in a similar way.
Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides
A divergent synthesis of pyrimidine and 8-oxo-purine nucleotides starting from a common prebiotic precursor that yields the β-ribo-stereochemistry found in the sugar phosphate backbone of biological nucleic acids is presented.
Purine Biosynthetic Intermediate-Containing Ribose-Phosphate Polymers as Evolutionary Precursors to RNA
It is proposed that the purine nucleobases arose in situ from simpler precursors attached to a ribose-phosphate backbone, and that the weaker and less specific intra- and interstrand interactions between these precursor were the forerunners to the base pairing and base stacking interactions of the modern RNA nucleobasing.
Borate-guided ribose phosphorylation for prebiotic nucleotide synthesis
A high-yield regioselective one-pot synthesis of ribose 5′-phosphate from an aqueous solution containing ribose, phosphate, urea, and borate by simple thermal evaporation is reported.
Synthesis of barbituric acid containing nucleotides and their implications for the origin of primitive informational polymers.
Preliminary evidence is provided that BA could have been a putative precursor of modern nucleobases, which could have be incorporated into primitive informational polymers that predated the molecules of an RNA world.


Selective derivatization and sequestration of ribose from a prebiotic mix.
This study demonstrates an approach for the preferential sequestration of ribose relative to other sugars that takes advantage of its greater reactivity, which is more reactive and degrades more rapidly compared with most other monosaccharides.
An efficient prebiotic synthesis of cytosine and uracil
In concentrated urea solution—such as might have been found in an evaporating lagoon or in pools on drying beaches on the early Earth—cyanoacetaldehyde reacts to form cytosine in yields of 30-50%, from which uracil can be formed by hydrolysis.
Prebiotic chemistry and the origin of the RNA world.
  • L. Orgel
  • Biology
    Critical reviews in biochemistry and molecular biology
  • 2004
The demonstration that ribosomal peptide synthesis is a ribozyme-catalyzed reaction makes it almost certain that there was once an RNA World, and a discussion of genetic systems simpler than RNA that might have "invented" RNA is discussed.
Prebiotic Formation of Cytidine Nucleotides
There seems to be no satisfactory concept for the genesis of polynucleotide templates in the presumed conditions of the primitive Earth, and some recent evidence suggests that natural nucleosides need not be direct precursors of the corresponding nucleotides and polyn DNA templates.
On the Prebiotic Synthesis of Ribonucleotides: Photoanomerisation of Cytosine Nucleosides and Nucleotides Revisited
The present study determined whether this low yield was the result of a low conversion or competing reaction pathways, and if an efficient means of anomerising this nucleoside or a derivative thereof were to be found, then the synthesis of one of the key β‐D‐nucleosides required to make RNA would be realised.
Prebiotic phosphorylation of nucleosides in formamide
A possible prebiotic phosphorylation method has been investigated in which formamide served as the reaction medium and the acidic dihydrogen phosphates and condensed hydrogen phosphates proved to be the best phosphorylating agents.
Studies in prebiotic synthesis. V. Synthesis and photoanomerization of pyrimidine nucleosides.
RNA: Prebiotic Product, or Biotic Invention?
Recent experimental work on the assembly of potential RNA precursors is reviewed, focusing on methods for stereoselective CC bond construction by aldolisation and related processes, and the relative accessibility of RNA and alternative nucleic acids is considered.
Structure of the photohydration products of cytidine and uridine.
  • N. Miller, P. Cerutti
  • Chemistry
    Proceedings of the National Academy of Sciences of the United States of America
  • 1968
reaction vessels and were arranged at a distance of 5 cm from the burner. The entire photochemical apparatus was immersed in a bath which was kept at 10?. The reaction solution was freed from oxygen