Synthesis of Pyrimidines and Triazines in Ice: Implications for the Prebiotic Chemistry of Nucleobases

Menor‐Salván, César; Ruiz‐Bermejo, Dra. Marta; Guzmán, Marcelo I.; Osuna‐Esteban, Susana; Veintemillas‐Verdaguer, S.

doi:10.1002/chem.200802656

Cited by 88 publications

(98 citation statements)

References 29 publications

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“…This ordering through assembly could then provide a catalyst for polymerization of protonucleic acid polymers, by aligning their functional groups. Additionally, these molecules are attractive protonucleic acid nucleobase candidates, as triaminopyrimidine forms glycosidic linkages with ribose to produce nucleosides in water, and barbituric acid, cyanuric acid, and melamine have been found in model prebiotic reactions [142,143].…”

Section: Selectionmentioning

confidence: 99%

A Chemical Engineering Perspective on the Origins of Life

Grover

Hsieh

et al. 2015

Processes

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Atoms and molecules assemble into materials, with the material structure determining the properties and ultimate function. Human-made materials and systems have achieved great complexity, such as the integrated circuit and the modern airplane. However, they still do not rival the adaptivity and robustness of biological systems. Understanding the reaction and assembly of molecules on the early Earth is a scientific grand challenge, and also can elucidate the design principles underlying biological materials and systems. This research requires understanding of chemical reactions, thermodynamics, fluid mechanics, heat and mass transfer, optimization, and control. Thus, the discipline of chemical engineering can play a central role in advancing the field. In this paper, an overview of research in the origins field is given, with particular emphasis on the origin of biopolymers and the role of chemical engineering phenomena. A case study is presented to highlight the importance of the environment and its coupling to the chemistry.

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Section: Selectionmentioning

confidence: 99%

A Chemical Engineering Perspective on the Origins of Life

Grover

Hsieh

et al. 2015

Processes

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“…At high concentrations, urea is considered an important prebiotic reactant in the synthesis of pyrimidines [22] [23]. Its role as a prebiotic reagent remains doubtful due to its instability at the high concentrations needed to act as a prebiotic intermediate [24].…”

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Thermal Wet Decomposition of Prussian Blue: Implications for Prebiotic Chemistry

Ruíz-Bermejo

Rogero

Menor‐Salván

et al. 2009

Chemistry & Biodiversity

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The complex salt named Prussian Blue, Fe4[Fe(CN)6]3 x 15 H2O, can release cyanide at pH > 10. From the point of view of the origin of life, this fact is of interest, since the oligomers of HCN, formed in the presence of ammonium or amines, leads to a variety of biomolecules. In this work, for the first time, the thermal wet decomposition of Prussian Blue was studied. To establish the influence of temperature and reaction time on the ability of Prussian Blue to release cyanide and to subsequently generate other compounds, suspensions of Prussian Blue were heated at temperatures from room temperature to 150 degrees at pH 12 in NH3 environment for several days. The NH3 wet decomposition of Prussian Blue generated hematite, alpha-Fe2O3, the soluble complex salt (NH4)4[Fe(CN6)] x 1.5 H2O, and several organic compounds, the nature and yield of which depend on the experimental conditions. Urea, lactic acid, 5,5-dimethylhydantoin, and several amino acids and carboxylic acids were identified by their trimethylsilyl (TMS) derivatives. HCN, cyanogen (C2N2), and formamide (HCONH2) were detected in the gas phase by GC/MS analysis.

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“…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 organic compounds found in biological systems have been synthesized in experiments of this nature; in particular, in the most recent study of Miller and coworkers (26), it was shown that a CO-CO 2 -N 2 -H 2 O atmosphere can give a variety of bioorganic compounds with yields comparable to those obtained from a strongly reducing atmosphere, suggesting that atmospheres containing carbon monoxide might therefore have been conducive to prebiotic synthesis and perhaps the origin of life.Theory and modeling have generally provided considerable insight (27) in prebiotic chemistry, particularly by studying the synthesis of simple organic molecules and the mechanisms and barriers of such reactions on substrates such as ice (28,29) or minerals (30,31). A remarkable theoretical study, based on ab initio molecular dynamics (AIMD), on prebiotic synthesis focused on the simulation of the effect of the pressure/temperature shock waves induced by the impact of bolides in the early Earth (17).…”

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confidence: 99%

Miller experiments in atomistic computer simulations

Saitta

Saija

2014

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

163

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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Synthesis of Pyrimidines and Triazines in Ice: Implications for the Prebiotic Chemistry of Nucleobases

Cited by 88 publications

References 29 publications

A Chemical Engineering Perspective on the Origins of Life

A Chemical Engineering Perspective on the Origins of Life

Thermal Wet Decomposition of Prussian Blue: Implications for Prebiotic Chemistry

Miller experiments in atomistic computer simulations

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