Possible pathway for prebiotic uracil synthesis by photodehydrogenation

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

doi:10.1038/263350a0

Cited by 42 publications

(20 citation statements)

References 19 publications

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“…We have found a novel feature in the photochemical reaction of DHO (Figure 6). In the irradiations of DHO through quartz glass with both high-or low-pressure mercury arc lamps, a large amount of DHU was produced, accompanied by relatively small quantities of orotic acid and uracil which might be formed by the known photodehydrogenation of the DHU (Chittenden and Schwartz, 1976). On the contrary, the irradiation through a Pyrex glass filter or the irradiation with the tungsten lamp afforded little DHU, but produced orotate and a lesser amount of uracil which was possibly produced by the photodecarboxylation of orotic acid (Ferris and Joshi, 1978).…”

Section: Resultsmentioning

confidence: 99%

“…In an aqueous solution of cyanoacetaldehyde and guanidine, diaminopyrimidine was formed and it was hydrolyzed to uracil via cytosine (FerNs et aL, 1974). Dihydrouracil (DHU) was synthesized from /~-alanine and urea under mild conditions and was further dehydrogenated by UV-irradiation on various supports to produce uracil (Chittenden and Schwartz, 1976). Hydrolysis of HCN oligomers produced 4,5-dihydroxypyrimidine, orotic acid, 5-hydroxyuracil and uracil as well as adenine and amino acids (Ferris et al, 1978b;Voet and Schwartz, 1982).…”

Section: Introductionmentioning

confidence: 99%

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Prebiotic synthesis of orotic acid parallel to the biosynthetic pathway

Yamagata

Sasaki

Takaoka

et al. 1990

Origins Life Evol Biosphere

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Prebiotic synthesis of orotic acid parallel to the biosynthetic pathway

Yamagata

Sasaki

Takaoka

et al. 1990

Origins Life Evol Biosphere

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“…These results indicate that the C5 position was unsubstituted in the pyrimidine ring. [31] The detection of undeuterated orotic acid, dihydroorotic-6[D], and malic acid support this mechanism. This conclusion suggests that the synthesis of pyrimidines follows three pathways.…”

Section: Productmentioning

confidence: 95%

A New Route for the Prebiotic Synthesis of Nucleobases and Hydantoins in Water/Ice Solutions Involving the Photochemistry of Acetylene

Menor‐Salván

Marín-Yaseli

2013

Chemistry A European J

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The origin of nucleobases and other heterocycles is a classic question in the chemistry of the origins of life. The construction of laboratory models for the abiotic synthesis of nitrogen heterocycles in plausible natural conditions also aids the understanding and prediction of chemical species in the Solar System. Here, we report a new explanation for the origin of hydantoins, purines, and pyrimidines in eutectic water/ice/urea solutions driven by ultraviolet irradiation (in the 185-254 nm range, UVC) of acetylene under anoxic conditions. An analysis of the products indicates the synthesis of hydantoin and 5-hydroxyhydantoin, the purines uric acid, xanthine, and guanine, and the pyrimidines uracil and cytosine. The synthesis occurred together with the photo-oxidation of bases in a complex process for which possible pathways are proposed. In conclusion, an acetylene-containing atmosphere could contribute to the origin of nucleobases in the presence of a urea/water system by an HCN-independent mechanism. The presence of ice has a dual role as a favorable medium for the synthesis of nucleobases and protection against degradation and as a source of free radicals for the synthesis of highly oxidized heterocycles. A mechanism for the origin of hydantoins and uracil from urea in plausible conditions for prebiotic chemistry is also proposed.

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“…Chittenden and Schwartz (1976) reported that the addition of montmorillonite increased the rate of adenine formation [32].…”

Section: Nucleic Acid Basesmentioning

confidence: 99%