Bringing Prebiotic Nucleosides and Nucleotides Down to Earth

Fiore, Michele; Strazewski, Peter

doi:10.1002/anie.201606232

Cited by 17 publications

(13 citation statements)

References 39 publications

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“…The isolated product was immediately subjected to the same conditions, which provided 5c after 7 days in pure form. This pathway via nitroso-pyrimidines thus affords 5c , the precursor for the canonical base A under plausible prebiotic conditions 20 . These conditions also lead to the parallel formation of the precursor to the ubiquitous 2-thiomethyl modification (ms 2 A), which is today found in all three domains of life.…”

Section: Resultsmentioning

confidence: 94%

Wet-dry cycles enable the parallel origin of canonical and non-canonical nucleosides by continuous synthesis

et al. 2018

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The molecules of life were created by a continuous physicochemical process on an early Earth. In this hadean environment, chemical transformations were driven by fluctuations of the naturally given physical parameters established for example by wet–dry cycles. These conditions might have allowed for the formation of (self)-replicating RNA as the fundamental biopolymer during chemical evolution. The question of how a complex multistep chemical synthesis of RNA building blocks was possible in such an environment remains unanswered. Here we report that geothermal fields could provide the right setup for establishing wet–dry cycles that allow for the synthesis of RNA nucleosides by continuous synthesis. Our model provides both the canonical and many ubiquitous non-canonical purine nucleosides in parallel by simple changes of physical parameters such as temperature, pH and concentration. The data show that modified nucleosides were potentially formed as competitor molecules. They could in this sense be considered as molecular fossils.

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Section: Resultsmentioning

confidence: 94%

Wet-dry cycles enable the parallel origin of canonical and non-canonical nucleosides by continuous synthesis

et al. 2018

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“…These are the two solvents most frequently considered in recent origin of life studies. [17][18][19][20][21][22] We will show that while aqueous solutions and lower temperatures could favor accumulation of 2',3' cyclic nucleotides over that of the 3',5' cyclic form, at higher temperatures and in formamide solvent 3',5' cyclic nucleotides are the thermodynamically preferred species. Thus, after a temperature drop, 23 initial cycles of polymerization leading to the first RNA molecules could indeed occur in a 3',5'-cyclic-nucleotide rich environment.…”

Section: Introductionmentioning

confidence: 90%

“…23 Note that such conditions are considered as a relevant context for prebiotic processes on early Earth not only by us 23 but also, e.g., by the so called "discontinuous synthesis model" of the origin of life advocated by the Benner group; 17,18 for another independent latest research highlight see Ref. 21. This was the reason why we have considered a much broader temperature range (from 363 up to 483 K) when studying solvation properties of our simplified cyclic nucleotide models in formamide.…”

Section: Stability Of Cyclic Nucleotides In Formamidementioning

confidence: 99%

Stability of 2′,3′ and 3′,5′ cyclic nucleotides in formamide and in water: a theoretical insight into the factors controlling the accumulation of nucleic acid building blocks in a prebiotic pool

Cassone

Šponer

Saija

et al. 2017

Phys. Chem. Chem. Phys.

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Synthesis of the first RNAs represents one of the cornerstones of the emergence of life. Recent studies demonstrated powerful scenarios of prebiotic synthesis of cyclic nucleotides in aqueous and formamide environments. This raised a question about their thermodynamic stability, a decisive factor determining their accumulation in the prebiotic pool. Here we performed ab initio molecular dynamics simulations at various temperatures in formamide and water to study the relative stabilities of the 2',3' and 3',5' isomers of cyclic nucleotides. The computations show that in an aqueous environment 2',3' cyclic nucleotides are more stable than their 3',5' counterparts at all temperatures up to the boiling point. In contrast, in formamide higher temperatures favor accumulation of the 3',5' cyclic form, whereas below about 400 K the 2',3' cyclic form becomes more stable. The latter observation is consistent with a formamide-based origin scenario suggesting that 3',5' cyclic nucleotides accumulated at higher temperatures subsequently allowed oligomerization reactions after fast cooling to lower temperatures. A statistical analysis of the geometrical parameters of the solutes indicates that thermodynamics of cyclic nucleotides in aqueous and formamide environments are dictated by the floppiness of the molecules rather than by the ring strain of the cyclic phosphodiester linkages.

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“…57 This approach is intriguing, but the benefits of N 9 -purination are offset by the formation of an inseparable mixture of α/β-furanoside and α/β-pyranoside nucleosides (even from a large excess of pure ribose 7 starting material) and poor selectivity for the natural β-furanosyl-ribonucleosides (8). 58 Furthermore, coupling formose-type sugar mixtures with N-formamidopyrimidines yield only analytically detectable amounts of the desired purine 8 (B = 3, <0.2%) interspersed amongst a multitude of other isomers and homologues. 57 Whether a similar strategy can be applied to the formation of pyrimidine ribonucleotides is currently unknown.…”

Section: Attempted Syntheses Of Ribonucleosides From Sugars and Nuclementioning

confidence: 99%

Prebiotic Systems Chemistry: Complexity Overcoming Clutter

Islam

Powner

2017

Chem

125

119

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SUMMARYLiving organisms are the most complex chemical system known to exist, yet exploit only a small constellation of universally conserved metabolites to support indefinite evolution. The conserved chemical simplicity belying biological diversity strongly indicates a unified origin of life. Thus, the chemical relationship between metabolites suggests that a simple set of predisposed chemical reactions predicated the appearance of life on Earth. Conversely, if prebiotic chemistry produces highly complex mixtures, this then implies that the feasibility of elucidating life's origins is an insurmountable task. Prebiotic systems chemistry, however, has recently been exploiting the chemical links between different metabolites to provide unprecedented scope for exploration of the origins of life, and an exciting new perspective on a 4 billion-year-old problem. At the heart of the systems approach is an understanding that individual classes of metabolites cannot be considered in isolation. This review highlights several recent advances suggesting that the canonical nucleotides and proteinogenic amino acids are predisposed chemical structures. KEYWORDSOrigins of life, prebiotic chemistry, systems chemistry, predisposed chemistry, RNA, nucleotides, amino acids, sugars, metabolism, crystallization. BIGGER PICTUREAdvancing our understanding of the spontaneous emergence of life requires innovation across scientific disciplines as broad as astrophysics to phylogenetics, yet the primacy of chemistry cannot be overestimated. Cellular life is a chemical system of awe-inspiring complexity yet, perhaps surprisingly, life exploits only a 2 small constellation of universally conserved metabolites working in concert to support indefinite evolution.The conserved chemical simplicity that belies biodiversity is a strong indication that a simple set of predisposed reactions predicated the sudden appearance of life on Earth. The wonder of nature's greatest feat of invention-the self-assembly of living cells-positions the origins of life as one of the greatest challenges in chemistry. Building chemical systems that can self-assemble, process information, control the transport and accumulation of chemicals, orchestrate reaction pathways, and ultimately self-replicate will no doubt have a major impact on evolving technology, but nature has had a 4 billion-year head start in implementing controlled chemical evolution, and the lessons to be learnt from its prior art merely await discovery. eTOCPrebiotic systems chemistry is providing unprecedented scope for exploring the origins of life and an exciting new perspective on a 4 billion-year-old problem. At the heart of this new systems approach is an understanding that individual classes of metabolites cannot be considered in isolation if the chemical origin of life on Earth is to be successfully elucidated. This review aims to highlight several recent advances that suggest the canonical nucleotides and proteinogenic amino acids are predisposed chemical structures.

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Bringing Prebiotic Nucleosides and Nucleotides Down to Earth

Cited by 17 publications

References 39 publications

Wet-dry cycles enable the parallel origin of canonical and non-canonical nucleosides by continuous synthesis

Wet-dry cycles enable the parallel origin of canonical and non-canonical nucleosides by continuous synthesis

Stability of 2′,3′ and 3′,5′ cyclic nucleotides in formamide and in water: a theoretical insight into the factors controlling the accumulation of nucleic acid building blocks in a prebiotic pool

Prebiotic Systems Chemistry: Complexity Overcoming Clutter

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