Synthesis of uracil and thymine under simulated prebiotic conditions

Schwartz, Alan W.; Chittenden, G. J. F.

doi:10.1016/0303-2647(77)90016-8

Cited by 46 publications

(23 citation statements)

References 9 publications

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“…Dihydrouracil and uracil participate in pyrimidine metabolism pathway (belong to ''nucleotide metabolism''), where 5,6-dihydrouracil and NADP+ are catalyzed by dihydropyrimidine dehydrogenase (DPD) to form uracil and NADPH+H+ [14,27]. They are also co-mentioned in many PubMed Abstracts such as [28,29,30,31,32,33,34,35,36,37]. Another two interactive compounds -dihydrouracil and dihydrothymine share a very similar structure, the only difference is that dihydrothymine has a methyl at the 5th position of the hexatomic ring while dihydrouracil has not [38].…”

Section: Evaluation Results By the 5-fold Cross-validationmentioning

confidence: 99%

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Chen

Huang

et al. 2011

PLoS ONE

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Given a compound, how can we effectively predict its biological function? It is a fundamentally important problem because the information thus obtained may benefit the understanding of many basic biological processes and provide useful clues for drug design. In this study, based on the information of chemical-chemical interactions, a novel method was developed that can be used to identify which of the following eleven metabolic pathway classes a query compound may be involved with: (1) Carbohydrate Metabolism, (2) Energy Metabolism, (3) Lipid Metabolism, (4) Nucleotide Metabolism, (5) Amino Acid Metabolism, (6) Metabolism of Other Amino Acids, (7) Glycan Biosynthesis and Metabolism, (8) Metabolism of Cofactors and Vitamins, (9) Metabolism of Terpenoids and Polyketides, (10) Biosynthesis of Other Secondary Metabolites, (11) Xenobiotics Biodegradation and Metabolism. It was observed that the overall success rate obtained by the method via the 5-fold cross-validation test on a benchmark dataset consisting of 3,137 compounds was 77.97%, which is much higher than 10.45%, the corresponding success rate obtained by the random guesses. Besides, to deal with the situation that some compounds may be involved with more than one metabolic pathway class, the method presented here is featured by the capacity able to provide a series of potential metabolic pathway classes ranked according to the descending order of their likelihood for each of the query compounds concerned. Furthermore, our method was also applied to predict 5,549 compounds whose metabolic pathway classes are unknown. Interestingly, the results thus obtained are quite consistent with the deductions from the reports by other investigators. It is anticipated that, with the continuous increase of the chemical-chemical interaction data, the current method will be further enhanced in its power and accuracy, so as to become a useful complementary vehicle in annotating uncharacterized compounds for their biological functions.

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Section: Evaluation Results By the 5-fold Cross-validationmentioning

confidence: 99%

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Chen

Huang

et al. 2011

PLoS ONE

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“…[33][34][35][36] Because of their biological importance, prebiotic synthetic routes for these nucleobases have been well explored. 37,38 It has been proposed that such N-containing macromolecules may be synthesized through complex reactions between abundant N-bearing species such as NH 3 or HCN and carbonaceous precursors in interstellar ice grains under the influence of UV photons and cosmic ray analogs (e.g., protons and electrons). [39][40][41][42][43] Recent laboratory experiments under interstellar-like conditions demonstrate the formation of uracil and cytosine upon UV irradiation of H 2 O:Pym and H 2 O:NH 3 :Pym ices, respectively.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic identification of fragment ions of DNA/RNA building blocks: the case of pyrimidine

Chatterjee

Dopfer

2020

Phys. Chem. Chem. Phys.

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“…This paper will focus exclusively on the abiotic extraterrestrial formation of thymine in ices containing astrophysically relevant components. For an introduction to potential terrestrial formation processes, please refer to papers by Schwartz and Chittenden (1977), as well as Choughuley et al (1977).…”

Section: Introductionmentioning

confidence: 99%

Thymine and Other Prebiotic Molecules Produced from the Ultraviolet Photo-Irradiation of Pyrimidine in Simple Astrophysical Ice Analogs

et al. 2013

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The informational subunits of RNA or DNA consist of substituted N-heterocyclic compounds that fall into two groups: those based on purine (C₅H₄N₄) (adenine and guanine) and those based on pyrimidine (C₄H₄N₂) (uracil, cytosine, and thymine). Although not yet detected in the interstellar medium, N-heterocycles, including the nucleobase uracil, have been reported in carbonaceous chondrites. Recent laboratory experiments and ab initio calculations have shown that the irradiation of pyrimidine in ices containing H₂O, NH₃, or both leads to the abiotic production of substituted pyrimidines, including the nucleobases uracil and cytosine. In this work, we studied the methylation and oxidation of pyrimidine in CH₃OH:pyrimidine, H₂O:CH₃OH:pyrimidine, CH₄:pyrimidine, and H₂O:CH₄:pyrimidine ices irradiated with UV photons under astrophysically relevant conditions. The nucleobase thymine was detected in the residues from some of the mixtures. Our results suggest that the abundance of abiotic thymine produced by ice photolysis and delivered to the early Earth may have been significantly lower than that of uracil. Insofar as the delivery of extraterrestrial molecules was important for early biological chemistry on early Earth, these results suggest that there was more uracil than thymine available for emergent life, a scenario consistent with the RNA world hypothesis.

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Synthesis of uracil and thymine under simulated prebiotic conditions

Cited by 46 publications

References 9 publications

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Spectroscopic identification of fragment ions of DNA/RNA building blocks: the case of pyrimidine

Thymine and Other Prebiotic Molecules Produced from the Ultraviolet Photo-Irradiation of Pyrimidine in Simple Astrophysical Ice Analogs

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