Prebiotic chemistry: A bioorganic perspective

Sutherland, John D.; Whitfield, J. N.

doi:10.1016/s0040-4020(97)00438-9

Cited by 95 publications

(52 citation statements)

References 86 publications

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“…Given that AICA and fAICA are not expected intermediates in the formation of purine nucleic bases through the classical routes of the pyrimidine ring, another mechanism of condensation of formamide is reasonably operative in the presence of montmorillonites. However, AICA has been proposed as a key intermediate (in addition to 5-amino-1H-imidazole-4-carbonitrile (AICN)) in the prebiotic synthesis of purines by polymerization of HCN [67], suggesting that its conversion to fAICA is a fundamental step in the synthesis of hypoxanthine [68].…”

Section: Chemiomimesis In Formamidementioning

confidence: 99%

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Formamide Chemistry and the Origin of Informational Polymers

Saladino

Crestini

Ciciriello

et al. 2007

Chemistry & Biodiversity

120

118

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Formamide (HCONH2) provides a chemical frame potentially affording all the monomeric components necessary for the formation of nucleic polymers. In the presence of the appropriate catalysts, and by moderate heating, formamide yields a complete set of nucleic bases, acyclonucleosides, and favors both phosphorylations and transphosphorylations. Physico-chemical conditions exist in which formamide favors the stability of the phosphoester bonds in nucleic polymers more than that of the same bonds in monomers. This property establishes 'thermodynamic niches' in which the polymeric forms are favored. The hypothesis that these specific attributes of formamide allowed the onset of prebiotic chemical equilibria capable of Darwinian evolution is discussed.

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Section: Chemiomimesis In Formamidementioning

confidence: 99%

“…Successive cyclization, formyl rearrangement, and elimination of formamide then affords AICN. Irrespective of the nature of the intermediates involved in these latter steps, the transformation of AICN to hypoxanthine through the successive synthesis of AICA and fAICA is a well-documented process [67] [68].…”

Section: Chemiomimesis In Formamidementioning

confidence: 99%

Formamide Chemistry and the Origin of Informational Polymers

Saladino

Crestini

Ciciriello

et al. 2007

Chemistry & Biodiversity

120

118

View full text Add to dashboard Cite

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“…Similarly, Orò demonstrated the spontaneous formation of nucleic acid bases from aqueous hydrogen cyanide subject to heating and/or spark discharges (5). Since then, a number of different hypotheses have been formulated to explain the synthesis, from simple molecules (water, ammonia, methane, carbon oxides), of simple organic molecules (formaldehyde, hydrogen cyanide, formic acid), and from the latter ones to biological monomers (amino acids, purines, pyrimidines) up the ladder of the complexity of life (6,7). However, a "standard model" explaining the emergence of larger and larger molecular assemblies is lacking.…”

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confidence: 99%

Miller experiments in atomistic computer simulations

Saitta

Saija

2014

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

170

147

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The celebrated Miller experiments reported on the spontaneous formation of amino acids from a mixture of simple molecules reacting under an electric discharge, giving birth to the research field of prebiotic chemistry. However, the chemical reactions involved in those experiments have never been studied at the atomic level. Here we report on, to our knowledge, the first ab initio computer simulations of Miller-like experiments in the condensed phase. Our study, based on the recent method of treatment of aqueous systems under electric fields and on metadynamics analysis of chemical reactions, shows that glycine spontaneously forms from mixtures of simple molecules once an electric field is switched on and identifies formic acid and formamide as key intermediate products of the early steps of the Miller reactions, and the crucible of formation of complex biological molecules.I n 1953, Miller reported (1) the surprising results he had achieved by the application of an electric discharge on a mixture of the gases CH 4 , NH 3 , H 2 O, and H 2 that simulated what was considered at the time as a model atmosphere for the primordial Earth. The result of this experiment was a substantial yield of a mixture of amino acids (2-4). Similarly, Orò demonstrated the spontaneous formation of nucleic acid bases from aqueous hydrogen cyanide subject to heating and/or spark discharges (5). Since then, a number of different hypotheses have been formulated to explain the synthesis, from simple molecules (water, ammonia, methane, carbon oxides), of simple organic molecules (formaldehyde, hydrogen cyanide, formic acid), and from the latter ones to biological monomers (amino acids, purines, pyrimidines) up the ladder of the complexity of life (6, 7). However, a "standard model" explaining the emergence of larger and larger molecular assemblies is lacking. Various sources of energy that might have initiated this synthesis have been suggested in the last 60 y, including UV irradiation both in extraterrestrial and terrestrial environments (8-11), hydrothermal energy from deep sea vents (12, 13), shock waves from meteorite impact (14-20), redox energy in the "iron−sulphur world" hypothesis (21), radioactive emission from uranium accumulation (22), and, of course, electric discharges originated by lightning, which motivated the Miller experiment, and are the inspiration of the present work. Despite the historical importance of Miller's experiments, no attempts have been made to explore the role of the electric field, traditionally considered merely in terms of just another thermal activation.A key aspect of that experiment was the formation of hydrogen cyanide, aldehydes, ketones, and amino acids, suggesting that the compounds were produced by the Strecker cyanohydrin reaction (23). Subsequent Miller-like experiments, run with other types and combinations of gases (24, 25) representing plausible geochemical conditions, produced other classes of basic building block molecules, namely sugars and nucleotides. To date, all of the major classes of...

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“…However, a mixture of activated nucleotides would need to have been available! Finally, when either the first replicative molecule, the template or one of its elements (nucleotides) is to be synthesized from the original building blocks, in particular the sugars that are constituents of nucleotides, a certain number of difficulties are encountered (Sutherland and Whitfield, 1997). First, synthesis of sugars from formaldehyde produces a complex mixture in which ribose is in low amounts.…”

Section: Marie-christine Maurelmentioning

confidence: 99%

5. Prebiotic Chemistry – Biochemistry – Emergence of Life (4.4–2 Ga)

et al. 2006

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Abstract. This chapter is devoted to a discussion about the difficulties and even the impossibility to date the events that occurred during the transition from non-living matter to the first living cells. Nevertheless, the attempts to devise plausible scenarios accounting for the emergence of the main molecular devices and processes found in biology are presented including the role of nucleotides at early stages (RNA world). On the other hand, hypotheses on the development of early metabolisms, comEarth, Moon, and Planets (2006) 98: 153-203 Ó Springer 2006

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Prebiotic chemistry: A bioorganic perspective

Cited by 95 publications

References 86 publications

Formamide Chemistry and the Origin of Informational Polymers

Formamide Chemistry and the Origin of Informational Polymers

Miller experiments in atomistic computer simulations

5. Prebiotic Chemistry – Biochemistry – Emergence of Life (4.4–2 Ga)

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