Prebiotic adenine synthesis via HCN oligomerization in ice

Schwartz, Alan W.; Joosten, H. F. P.; Voet, Andries B.

doi:10.1016/0303-2647(82)90003-x

Cited by 61 publications

(36 citation statements)

References 13 publications

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“…This very concentrated solution slowly deposits a typical dark HCN polymer. Schwartz and his coworkers showed that adenine could be obtained in 0.004% yield by hydrolysis of this polymer or in 0.02% yield if glycolonitrile was added to the reaction mixture before freezing (Schwartz et al, 1982). Miller and his coworkers have obtained very similar results (Miyakawa et al, 2002a(Miyakawa et al, , 2002b.…”

Section: Purine Synthesismentioning

confidence: 84%

Prebiotic Chemistry and the Origin of the RNA World

Orgel

2004

Critical Reviews in Biochemistry and Molecular Biology

907

248

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The demonstration that ribosomal peptide synthesis is a ribozyme-catalyzed reaction makes it almost certain that there was once an RNA World. The central problem for origin-of-life studies, therefore, is to understand how a protein-free RNA World became established on the primitive Earth. We first review the literature on the prebiotic synthesis of the nucleotides, the nonenzymatic synthesis and copying of polynucleotides, and the selection of ribozyme catalysts of a kind that might have facilitated polynucleotide replication. This leads to a brief outline of the Molecular Biologists' Dream, an optimistic scenario for the origin of the RNA World. In the second part of the review we point out the many unresolved problems presented by the Molecular Biologists' Dream. This in turn leads to a discussion of genetic systems simpler than RNA that might have "invented" RNA. Finally, we review studies of prebiotic membrane formation.

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Section: Purine Synthesismentioning

confidence: 84%

Prebiotic Chemistry and the Origin of the RNA World

Orgel

2004

Critical Reviews in Biochemistry and Molecular Biology

907

248

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“…This freezing procedure was used to concentrate the HCN in the tetramer synthesis experiments, but adenine was not looked for (Sanchez et al 1966). Freezing at −2°C of 0.01 M HCN was effective in producing adenine, but only in the presence of NH 4 OH (Schwartz et al 1982).…”

Section: Resultsmentioning

confidence: 99%

Production of Guanine from NH4CN Polymerizations

1999

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The synthesis of adenine from the polymerization of concentrated ammonium cyanide solutions is well known. We show here that guanine is also produced by this reaction but at yields ranging from 10 to 40 times less than that of adenine. This synthesis is effective at both +80 and -20 degrees C. Since high concentrations of NH(4)CN are obtainable only by freezing, this prebiotic synthesis would be applicable to frozen regions of the primitive Earth, the Jovian satellite Europa and other icy satellites, and the parent body of the Murchison meteorite.

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“…Interestingly, the plausibility of ice as a matrix has also been discussed with respect to other aspects about the origin of metabolism. Ice may have helped to establish compartmentalization, essential for any form of metabolism, and it enables the synthesis of nucleobases (29)(30)(31)(32) and supports a nonenzymatic polymerization and a template-directed mechanism for copying RNA (33)(34)(35). Freeze-thaw cycles thus could have helped to achieve both the copying of nucleic acids and nonenzymatic reactions that form the metabolic components of RNA and DNA.…”

Section: Discussionmentioning

confidence: 99%

Nonenzymatic gluconeogenesis-like formation of fructose 1,6-bisphosphate in ice

Messner

Driscoll

Piedrafita

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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The evolutionary origins of metabolism, in particular the emergence of the sugar phosphates that constitute glycolysis, the pentose phosphate pathway, and the RNA and DNA backbone, are largely unknown. In cells, a major source of glucose and the large sugar phosphates is gluconeogenesis. This ancient anabolic pathway (re-)builds carbon bonds as cleaved in glycolysis in an aldol condensation of the unstable catabolites glyceraldehyde 3-phosphate and dihydroxyacetone phosphate, forming the much more stable fructose 1,6-bisphosphate. We here report the discovery of a nonenzymatic counterpart to this reaction. The in-ice nonenzymatic aldol addition leads to the continuous accumulation of fructose 1,6-bisphosphate in a permanently frozen solution as followed over months. Moreover, the in-ice reaction is accelerated by simple amino acids, in particular glycine and lysine. Revealing that gluconeogenesis may be of nonenzymatic origin, our results shed light on how glucose anabolism could have emerged in early life forms. Furthermore, the amino acid acceleration of a key cellular anabolic reaction may indicate a link between prebiotic chemistry and the nature of the first metabolic enzymes.T he metabolic network is a large cellular system that generates life's building blocks including amino acids, nucleotides, and lipids. Most of the metabolic pathways that participate in this network are well understood, but their evolutionary origin remains an unsolved problem. The network contains many reactive and unstable intermediates, yet its topological organization is widely conserved and considered ancient. It has therefore been extensively debated to what extent this structure could be the result of Darwinian selection and thus be of postgenetic origin or whether the metabolic network topology dates back to a nonenzymatic chemistry (1-4). A series of recently discovered chemical networks provide evidence for the latter. In the presence of simple inorganic ions as found in Archean sediment, and under conditions that are reminiscent of the chemistry that operates in cells, nonenzymatic reactions replicate essential topological elements of the most central metabolic pathways. Nonenzymatic chemical reactions currently replicate glycolysis (including the EmbdenMeyerhof-Parnas pathway, the Entner-Doudoroff pathway, and their many variants), the pentose phosphate pathway, the catabolic reactions of the TCA cycle, and the formation of the methyl group donor S-adenosylmethionine (5-8). Moreover, reactions of glycolysis and the pentose phosphate pathway, as well as reactions replicating the oxidative TCA cycle, can each occur in distinct but unifying reaction milieus, respectively. This implies that simple inorganic catalysts were shaping the topological structure of the metabolic network. In other words, the reactions that sugar phosphates undergo in the presence of the highest concentrated transition metal in Archean sediment [Fe(II)] and the reactions that TCA intermediates undergo in the presence of sulfate radicals are reflected i...

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Prebiotic adenine synthesis via HCN oligomerization in ice

Cited by 61 publications

References 13 publications

Prebiotic Chemistry and the Origin of the RNA World

Prebiotic Chemistry and the Origin of the RNA World

Production of Guanine from NH4CN Polymerizations

Nonenzymatic gluconeogenesis-like formation of fructose 1,6-bisphosphate in ice

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