Uracil

[2] The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid.

[3] Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein;[4] it was also found in bovine thymus and spleen, herring sperm, and wheat germ.

[6] Uracil that was formed extraterrestrially has been detected in the Murchison meteorite,[7] in near-Earth asteroid Ryugu,[8] and possibly on the surface of the moon Titan.

[9] It has been synthesized under cold laboratory conditions similar to outer space, from pyrimidine embedded in water ice and exposed to ultraviolet light.

[6] Uracil undergoes amide-imidic acid tautomeric shifts because any nuclear instability the molecule may have from the lack of formal aromaticity is compensated by the cyclic-amidic stability.

This enzyme would therefore recognize and cut out both types of uracil – the one incorporated naturally, and the one formed due to cytosine deamination, which would trigger unnecessary and inappropriate repair processes.

Uracil-containing DNA still exists, for example in: Organisms synthesize uracil, in the form of uridine monophosphate (UMP), by decarboxylating orotidine 5'-monophosphate (orotidylic acid).

In contrast to the purine nucleotides, the pyrimidine ring (orotidylic acid) that leads uracil is synthesized first and then linked to ribose phosphate, forming UMP.

[17] In 2009, NASA scientists reported having produced uracil from pyrimidine and water ice by exposing it to ultraviolet light under space-like conditions.

[18] In 2014, NASA scientists reported that additional complex DNA and RNA organic compounds of life, including uracil, cytosine and thymine, have been formed in the laboratory under outer space conditions, starting with ice, pyrimidine, ammonia, and methanol, which are compounds found in astrophysical environments.

[19] Pyrimidine, like polycyclic aromatic hydrocarbons (PAHs), a carbon-rich chemical found in the Universe, may have been formed in red giants or in interstellar dust and gas clouds.

[20] Based on 12C/13C isotopic ratios of organic compounds found in the Murchison meteorite, it is believed that uracil, xanthine, and related molecules can also be formed extraterrestrially.

[7] Data from the Cassini mission, orbiting in the Saturn system, suggests that uracil is present in the surface of the moon Titan.

[9] In 2023, uracil was observed in a sample from 162173 Ryugu, a near-Earth asteroid, with no exposure to Earth's biosphere, giving further evidence for synthesis in space.

[5] Uracil readily undergoes addition to ribose sugars and phosphates to partake in synthesis and further reactions in the body.

[21] Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates.

[33] Uracil derivatives are more often used as antiphotosynthetic herbicides, destroying weeds in cotton, sugar beet, turnips, soya, peas, sunflower crops, vineyards, berry plantations, and orchards.

Structural formula of uracil
Structural formula of uracil
Ball-and-stick model of uracil
Ball-and-stick model of uracil
Space-filling model of uracil
Space-filling model of uracil
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability (yellow): no hazard code Special hazards (white): no code
Uracil tautomers : Amide or lactam structure (left) and imide or lactim structure (right)
Chemical structure of uridine