Nucleoside Synthesis under Potentially Prebiotic Conditions

Reid, Caroline M.; Orgel, Leslie E.; Ponnamperuma, Cyril

doi:10.1038/216936a0

Cited by 25 publications

(11 citation statements)

References 3 publications

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“…Experimentally, Oró demonstrated a plausible prebiotic synthesis of deoxyribose starting with simple aldehydes but in about 3 % yield [9] . The synthesis of deoxyadenosine (7 % yield) was reported by Ponnamperuma starting from adenine and 2‐deoxyribose [10] . Sutherland in 2014, [11] and later Clarke in 2017, [12] showed the synthesis of deoxyribose under prebiotic conditions.…”

Section: Introductionmentioning

confidence: 89%

Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA

2021

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Recent demonstrations of RNA–DNA chimeras (RDNA) enabling RNA and DNA replication, coupled with prebiotic co‐synthesis of deoxyribo‐ and ribo‐nucleotides, have resurrected the hypothesis of co‐emergence of RNA and DNA. As further support, we show that diamidophosphate (DAP) with 2‐aminoimidazole (amido)phosphorylates and oligomerizes deoxynucleosides to form DNA—under conditions similar to those of ribonucleosides. The pyrimidine deoxynucleoside 5′‐O‐amidophosphates are formed in good (≈60 %) yields. Intriguingly, the presence of pyrimidine deoxynucleos(t)ides increased the yields of purine deoxynucleotides (≈20 %). Concomitantly, oligomerization (≈18–31 %) is observed with predominantly 3′,5′‐phosphodiester DNA linkages, and some (<5 %) pyrophosphates. Combined with previous observations of DAP‐mediated chemistries and the constructive role of RDNA chimeras, the results reported here help set the stage for systematic investigation of a systems chemistry approach of RNA–DNA coevolution.

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Section: Introductionmentioning

confidence: 89%

Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA

2021

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“…21 Their composition reveals that formamide, together with cyanhydric acid (HCN), isocyanate (HNCO) and water (H 2 O), constitutes the most abundant molecules containing the four biologically relevant elements, O, N, H and C. [22][23][24] Hence, formamide seems to play a positive role as a synthon for purine and pyrimidine nucleobases acting as a prebiotic precursor. [25][26][27][28] The efficiency of formamide chemistry in the origin of the informational polymers strictly depends on the metal oxides and minerals used in its condensation. 29 The reactivity of this molecule has also attracted much attention because it constitutes a suitable model to study the reactivity of larger biochemical compounds.…”

Section: Introductionmentioning

confidence: 99%

Modeling the interactions between peptide functions and Sr2+: formamide–Sr2+ reactions in the gas phase

Eizaguirre

Mó

Yáñez

et al. 2011

Phys. Chem. Chem. Phys.

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The interactions between formamide, which can be considered a prototype of a peptide function, and Sr(2+) have been investigated by combining nanoelectrospray ionization/mass spectrometry techniques and G96LYP DFT calculations. For Sr an extended LANL2DZ basis set was employed, together with a 6-311+G(3df,2p) basis set expansion for the remaining atoms of the system. The observed reactivity seems to be dominated by the Coulomb explosion process yielding [SrOH](+) + [HNCH](+), which are the most intense peaks in the MS/MS spectra. Nevertheless, additional peaks corresponding to the loss of HNC and CO indicate that the association of Sr(2+) to water or to ammonia leads to long-lived doubly charged species detectable in the timescale of these experimental techniques. The topology of the calculated potential energy surface permits us to establish the mechanisms behind these processes. Although the interaction between the neutral base and Sr(2+) is essentially electrostatic, the polarization triggered by the doubly charged metal ion results in the activation of several bonds, and favors different proton transfer mechanisms required for the formation of the [SrOH](+), [SrOH(2)](2+) and [SrNH(3)](2+) products.

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“…Aqueous solutions of carbohydrates are reported to be unstable [38]. Reid and Orgel observed that diluted solutions of carbohydrates under prebiotic conditions degrade within hours or days [60] and ribose decomposes even at low temperature and neutral pH (44 years at 0< T ≤ 150 • C) [42]. None of the experiments contain, however, any information about the quality of the water, used for the solutions.…”

Section: Carbohydratesmentioning

confidence: 99%

The Role of Carbohydrates at the Origin of Homochirality in Biosystems

Toxværd

2013

Orig Life Evol Biosph

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Pasteur has demonstrated that the chiral components in a racemic mixture can separate in homochiral crystals. But with a strong chiral discrimination the chiral components in a concentrated mixture can also phase separate into homochiral fluid domains, and the isomerization kinetics can then perform a symmetry breaking into one thermodynamical stable homochiral system. Glyceraldehyde has a sufficient chiral discrimination to perform such a symmetry breaking.The requirement of a high concentration of the chiral reactant(s) in an aqueous solution in order to perform and maintain homochirality; the appearance of phosphorylation of almost all carbohydrates in the central machinery of life; the basic ideas that the biochemistry and the glycolysis and gluconeogenesis contain the trace of the biochemical evolution, all point in the direction of that homochirality was obtained just after-or at a phosphorylation of the very first products of the formose reaction, at high concentrations of the reactants in phosphate rich compartments in submarine hydrothermal vents.A racemic solution of D,L-glyceraldehyde-3-phosphate could be the template for obtaining homochiral D-glyceraldehyde-3-phosphate(aq) as well as L-amino acids.

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Nucleoside Synthesis under Potentially Prebiotic Conditions

Cited by 25 publications

References 3 publications

Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA

Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA

Modeling the interactions between peptide functions and Sr2+: formamide–Sr2+ reactions in the gas phase

The Role of Carbohydrates at the Origin of Homochirality in Biosystems

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