Free radical pathways for the prebiotic formation of xanthine and isoguanine from formamide

Jeilani, Yassin A.; Nguyen, Huyen Thi; Cardelino, Beatriz H.; Nguyen, Minh Tho

doi:10.1016/j.cplett.2014.02.053

Cited by 19 publications

(50 citation statements)

References 33 publications

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“…30 and 31) through the involvement of the catalytic cNH 2 /NH 3 pair. 20,29,30 We believe that our proposed pathways will provide fundamental insights about underlying mechanisms of formation of non-canonical nucleobases (components of preRNA) and hopefully inspire future experimental studies in this direction.…”

Section: Introductionmentioning

confidence: 88%

“…This method was chosen in synchrony with recent computational studies on radical pathways of prebioticallyimportant reactions. 13,20,[29][30][31] Stationary points on the reaction surfaces were characterized as minima (i.e. reactants, intermediates or products) or rst-order saddle points (i.e.…”

Section: Computational Detailsmentioning

confidence: 99%

“…1 and S2 †). 18 is then attacked by NH 3 through 9.5 kcal mol À1 barrier to give 19, which is converted into its radical form (20) by passing a low (3.4 kcal mol À1 ) barrier. 20 can adopt two conformations (i.e.…”

Section: Formation Of MMmentioning

confidence: 99%

“…19 Subsequent theoretical investigations suggest the involvement of radicals in such prebiotic reactions. 20,21 Given the relevance of BA, MM, CA and TAP in context of the formation of prebiotic supramolecular assemblies, [3][4][5][6][7][8] it is reasonable to hypothesize that these heterocycles might have formed and then coexisted in a common prebiotic environment, which would have ultimately led to their assembly presumably by non-covalent interactions. Indeed, such a scenario can be considered as a preliminary step for the formation of subsequent more-evolved, covalently-linked prebiotic polymers similar to extant nucleic acids.…”

Section: Introductionmentioning

confidence: 99%

“…24 The proposed pathways include prebiotic heterocycle formation through reaction of cyanamide, urea (prebiotically derived from cyanamide 25 ) or malonic acid (that can, in turn, be obtained from urea 14 ) with each other or with other prebiotically-relevant species such as malononitrile, 26,27 cNH 2 (ref. 11, 12 and 28) cOH, 13,20,29,30 and NH 3 (ref. 30 and 31) through the involvement of the catalytic cNH 2 /NH 3 pair.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Radical pathways for the formation of non-canonical nucleobases in prebiotic environments

Kaur

Sharma

2019

RSC Adv.

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Section: Introductionmentioning

confidence: 88%

Section: Computational Detailsmentioning

confidence: 99%

Section: Formation Of MMmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Radical pathways for the formation of non-canonical nucleobases in prebiotic environments

Kaur

Sharma

2019

RSC Adv.

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Emergence of the First Catalytic Oligonucleotides in a Formamide‐Based Origin Scenario

Šponer

Nováková

et al. 2016

Chemistry A European J

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50 years after the historical Miller-Urey experiment, the formamide-based scenario is perhaps the most powerful concurrent hypothesis for the origin of life on our planet besides the traditional HCN-based concept. The information accumulated during the last 15 years in this topic is astonishingly growing and nowadays the formamide-based model represents one of the most complete and coherent pathways leading from simple prebiotic precursors up to the first catalytically active RNA molecules. In this work, we overview the major events of this long pathway that have emerged from recent experimental and theoretical studies, mainly concentrating on the mechanistic, methodological, and structural aspects of this research.

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Photophysical Characterization of Isoguanine in a Prebiotic‐Like Environment

Ortín-Fernández

Caldero-Rodríguez

Crespo‐Hernández

et al. 2023

Chemistry A European J

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It is intriguing how a mixture of organic molecules survived the prebiotic UV fluxes and evolved into the actual genetic building blocks. Scientists are trying to shed light on this issue by synthesizing nucleic acid monomers and their analogues under prebiotic Era-like conditions and by exploring their excited state dynamics. To further add to this important body of knowledge, this study discloses new insights into the photophysical properties of protonated isoguanine, an isomorph of guanine, using steady-state and femtosecond broadband transient absorption spectroscopies, and quantum mechanical calculations. Protonated isoguanine decays in ultrafast time scales following 292 nm excitation, consistently with the barrierless paths connecting the bright S 1 (ππ*) state with different internal conversion funnels. Complementary calculations for neutral isoguanine predict similar photophysical properties. These results demonstrate that protonated isoguanine can be considered photostable in contrast to protonated guanine, which exhibits 40-fold longer excited state lifetimes.

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Free radical pathways for the prebiotic formation of xanthine and isoguanine from formamide

Cited by 19 publications

References 33 publications

Radical pathways for the formation of non-canonical nucleobases in prebiotic environments

Radical pathways for the formation of non-canonical nucleobases in prebiotic environments

Emergence of the First Catalytic Oligonucleotides in a Formamide‐Based Origin Scenario

Photophysical Characterization of Isoguanine in a Prebiotic‐Like Environment

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