Neuere Methoden der präparativen organischen Chemie II. 16. Synthesen mit Säure‐amiden, insbesondere mit Formamid

Bredereck, Hellmut; Gompper, Rudolf; Schuh, H.; Theilig, Gerhard

doi:10.1002/ange.19590712402

Cited by 94 publications

(9 citation statements)

References 49 publications

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“…All these compounds are possible intermediates in the prebiotic synthesis of nucleic acids, thus increasing the network of possible transformations [64,65]. The chemical potential of H 2 NCHO in prebiotic chemistry was, for a long period of time, considered to be limited to the synthesis of a small number of heterocycles including, as a nucleic base, only adenine [66,67]. Seminal studies have shown that formamide oligomers, ammonia, and HCN were involved in the mechanism of formation of adenine by a multi-steps condensation process [68,69].…”

Section: Syntheses Of Nucleic Bases From Formamidementioning

confidence: 99%

Formamide and the origin of life

Saladino

Crestini

Pino

et al. 2012

Physics of Life Reviews

260

234

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The complexity of life boils down to the definition: "self-sustained chemical system capable of undergoing Darwinian evolution" (Joyce, 1994) [1]. The term "self-sustained" implies a set of chemical reactions capable of harnessing energy from the environment, using it to carry out programmed anabolic and catabolic functions. We briefly present our opinion on the general validity of this definition.Running anabolic and catabolic functions entails complex chemical information whose stability, reproducibility and evolution constitute the core of what is dubbed genetics.Life as-we-know-it is made of the intimate interaction of metabolism and genetics, both built around the chemistry of the most common elements of the Universe (hydrogen, oxygen, nitrogen, carbon). Other elements like phosphorus and sulphur play important but ancillary and potentially replaceable roles.The reproducible interaction of metabolic and genetic cycles results in the hypercycles of organization and de-organization of chemical information that we consider living entities. In order to approach the problem of the origin of life it is therefore reasonable to start from the assumption that both metabolism and genetics had a common origin, shared a common chemical frame, were embedded in physical-chemical conditions favourable for the onset of both.The most abundant three-atoms organic compound in interstellar environment is hydrogen cyanide HCN, the most abundant three-atoms inorganic compound is water H 2 O. The combination of the two results in the formation of formamide H 2 NCOH. We have explored the chemistry of formamide in conditions compatible with the synthesis and the stability of compounds of potential pre-genetic and pre-metabolic interest. We discuss evidence showing (i) that all the compounds necessary for the build-up of nucleic acids are easily obtained abiotically, (ii) that essentially all the steps leading to the spontaneous generation of RNA are abiotically possible, (iii) that the key compounds of extant metabolic cycles are obtained in the same chemical frame, often in the same test tube.How close are these observations to a plausible scenario for the origin of life?

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Section: Syntheses Of Nucleic Bases From Formamidementioning

confidence: 99%

Formamide and the origin of life

Saladino

Crestini

Pino

et al. 2012

Physics of Life Reviews

260

234

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“…Later he and other researchers also managed to synthesize further nucleobases from the same or similar starting materials [3,[57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72]. The problem with these reactions is that the quite high educt concentrations needed can only be reached via freezing of aqueous solutions of the educt [68,73], which is a rather improbable process on a hot primordial earth with volcanism and meteoritic impacts that had just cooled down to temperatures below the boiling point of water.…”

Section: Nucleobases and Ribosementioning

confidence: 95%

Prebiotic Chemistry: The Amino Acid and Peptide World

Plankensteiner¹,

Reiner²,

Rode

2005

COC

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In this review the idea of a "Peptide/Protein World" preceding the widely rooted idea of the "RNA world" is presented and elaborated. To support this idea, the formation of the building blocks of nucleic acids and peptides and their assembly to biopolymers in a primordial earth scenario is discussed. Furthermore, chemical stability problems of the building blocks and the assembled biomolecules are presented, and finally their ability to efficiently replicate and chemically evolve is argued. Taking into account various problems in all these areas for nucleic acids and nucleotides, the idea of the "Peptide/Protein World" is brought up, stating that peptides and proteins would have come first in chemical evolution with an "RNA world" appearing only later with the protective help of protein shells.

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“…The specific question addressed here concerns the synthesis of monomers under these conditions in the presence of formamide, a simple onecarbon chemical precursor, and the rate at which RNA is hydrolyzed under the same conditions. The synthesis of nitrogen-containing heterocycles from formamide under homogeneous conditions has been reported by Bredereck et al (1956Bredereck et al ( , 1959, Ivanov and Vladovska (1978), Yamada and Okamoto (1972), Yamada et al (1978) and by Miyakawa et al (2002). The prebiotic chemistry of formamide in the presence of minerals has been also recently investigated (Saladino et al 2007;Saladino et al 2009).…”

mentioning

confidence: 92%

Catalytic effects of Murchison Material: Prebiotic Synthesis and Degradation of RNA Precursors

Saladino

Crestini

Cossetti

et al. 2011

Orig Life Evol Biosph

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Mineral components of the Murchison meteorite were investigated in terms of potential catalytic effects on synthetic and hydrolytic reactions related to ribonucleic acid. We found that the mineral surfaces catalyzed condensation reactions of formamide to form carboxylic acids, amino acids, nucleobases and sugar precursors. These results suggest that formamide condensation reactions in the parent bodies of carbonaceous meteorites could give rise to multiple organic compounds thought to be required for the emergence of life. Previous studies have demonstrated similar catalytic effects for mineral assemblies likely to have been present in the early Earth environment. The minerals had little or no effect in promoting hydrolysis of RNA (24mer of polyadenylic acid) at 80°C over a pH range from 4.2 to 9.3. RNA was most stable in the neutral pH range, with a half-life ~5 h, but at higher and lower pH ranges the half-life decreased to ~1 h. These results suggest that if RNA was somehow incorporated into a primitive form of RNA-based thermophilic life, either it must be protected from random hydrolytic events, or the rate of synthesis must exceed the rate of hydrolysis.

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Neuere Methoden der präparativen organischen Chemie II. 16. Synthesen mit Säure‐amiden, insbesondere mit Formamid

Cited by 94 publications

References 49 publications

Formamide and the origin of life

Formamide and the origin of life

Prebiotic Chemistry: The Amino Acid and Peptide World

Catalytic effects of Murchison Material: Prebiotic Synthesis and Degradation of RNA Precursors

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