Open Access Articles- Top Results for Uracil
Research & Reviews: Journal of Pharmacology and Toxicological StudiesEvaluation of Anti-Cancer Activity of Kigelia africana on EAC Induced Solid Tumors
Journal of Clinical ToxicologyCardiotoxicity in Asymptomatic Patients Receiving Adjuvant 5-fluorouracil
Journal of Chromatography & Separation TechniquesSimultaneous Quantification of 5-Fluorouracil and Leucovorin in Pharmaceutical Dosage Form and Human Spiked Plasma by Using RPHPLC Method
Journal of Clinical & Cellular ImmunologyImmunohistochemical Study of the Effect of Chamomile Extract on 5-Fluorouracil Induced Intestinal Mucositis in Albino Rats
Journal of Microbial & Biochemical TechnologyStrain Improvement of Brevibacillus borostelensis R1 for Optimization of α-Amylase Production by Mutagens
|Structural formula of uracil|
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Uracil // (U) is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. Uracil could be considered a demethylated form of thymine.
Uracil is a common and naturally occurring pyrimidine derivative. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein; it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.
Studies reported in 2008, based on 12C/13C isotopic ratios of organic compounds found in the Murchison meteorite, suggested that uracil, xanthine and related molecules were formed extraterrestrially.
In RNA, uracil base-pairs with adenine and replaces thymine during DNA transcription. Methylation of uracil produces thymine. In DNA, the evolutionary substitution of thymine for uracil may have increased DNA stability and improved the efficiency of DNA replication. Uracil pairs with adenine through hydrogen bonding. When base pairing with adenine, uracil acts as both a hydrogen bond acceptor and a hydrogen bond donor. In RNA, uracil binds with a ribose sugar to form the ribonucleoside uridine. When a phosphate attaches to uridine, uridine 5'-monophosphate is produced.
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. The amide tautomer is referred to as the lactam structure, while the imidic acid tautomer is referred to as the lactim structure. These tautomeric forms are predominant at pH 7. The lactam structure is the most common form of uracil.
Uracil also recycles itself to form nucleotides by undergoing a series of phosphoribosyltransferase reactions. Degradation of uracil produces the substrates aspartate, carbon dioxide, and ammonia.
- C4H4N2O2 → H3NCH2CH2COO− + NH4+ + CO2
Uracil is a weak acid. The first site of ionization of uracil is not known. The negative charge is placed on the oxygen anion and produces a pKa of less than or equal to 12. The basic pKa = -3.4, while the acidic pKa = 9.389. In the gas phase, uracil has 4 sites that are more acidic than water.
In a scholarly article published in October 2009, NASA scientists reported having reproduced uracil from pyrimidine by exposing it to ultraviolet light under space-like conditions. This suggests that one possible natural original source for uracil in the RNA world could have been panspermia. More recently, in March 2015, NASA scientists reported that, for the first time, additional complex DNA and RNA organic compounds of life, including uracil, cytosine and thymine, have been formed in the laboratory under outer space conditions, using starting chemicals, such as pyrimidine, found in meteorites. Pyrimidine, like polycyclic aromatic hydrocarbons (PAHs), the most carbon-rich chemical found in the Universe, may have been formed in red giants or in interstellar dust and gas clouds, according to the scientists.
There are many laboratory syntheses of uracil available. The first reaction is the simplest of the syntheses, by adding water to cytosine to produce uracil and ammonia. The most common way to synthesize uracil is by the condensation of maleic acid with urea in fuming sulfuric acid as seen below also. Uracil can also be synthesized by a double decomposition of thiouracil in aqueous chloroacetic acid.
- C4H5N3O + H2O → C4H4N2O2 + NH3
- COOH(CH)2COOH + NH2CONH2 → C4H4N2O2 + 2 H2O + CO
Uracil readily undergoes regular reactions including oxidation, nitration, and alkylation. While in the presence of phenol (PhOH) and sodium hypochlorite (NaOCl), uracil can be visualized in ultraviolet light. Uracil also has the capability to react with elemental halogens because of the presence of more than one strongly electron donating group.
Uracil readily undergoes addition to ribose sugars and phosphates to partake in synthesis and further reactions in the body. Uracil becomes uridine, uridine monophosphate (UMP), uridine diphosphate (UDP), uridine triphosphate (UTP), and uridine diphosphate glucose (UDP-glucose). Each one of these molecules is synthesized in the body and has specific functions.
When uracil reacts with anhydrous hydrazine, a first-order kinetic reaction occurs and the uracil ring opens up. If the pH of the reaction increases to >10.5, the uracil anion forms, making the reaction go much more slowly. The same slowing of the reaction occurs if the pH decreases, because of the protonation of the hydrazine. The reactivity of uracil remains unchanged, even if the temperature changes.
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. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants. UMP controls the activity of carbamoyl phosphate synthetase and aspartate transcarbamoylase in plants, while UDP and UTP requlate CPSase II activity in animals. UDP-glucose regulates the conversion of glucose to galactose in the liver and other tissues in the process of carbohydrate metabolism. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes. It can also increase the risk for cancer in cases in which the body is extremely deficient in folate. The deficiency in folate leads to increased ratio of deoxyuracilmonophosphates (dUMP)/deoxythyminemonophosphates (dTMP) and uracil misincorporation into DNA and eventually low production of DNA.
Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine is reacted with uracil, 5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetabolite) used to masquerade as uracil during the nucleic acid replication process. Because 5-Fluorouracil is similar in shape to, but does not undergo the same chemistry as, uracil, the drug inhibits RNA replication enzymes, thereby blocking RNA synthesis and stopping the growth of cancerous cells. Uracil can also be used in the synthesis of caffeine 
Uracil can be used to determine microbial contamination of tomatoes. The presence of uracil indicates lactic acid bacteria contamination of the fruit. Uracil derivatives containing a diazine ring are used in pesticides. 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.
In yeast, uracil concentrations are inversely proportional to uracil permease.
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- Robert Behrend (1885) "Versuche zur Synthese von Körpern der Harnsäurereihe" (Experiments on the synthesis of substances in the uric acid series), Annalen der Chemie, 229 : 1-44. From page 11: "Dasselbe stellt sich sonach als Methylderivat der Verbindung: [molecular structure of uracil] welche ich willkürlich mit dem Namen Uracil belege, dar." (The same [compound] is therefore represented as the methyl derivative of the compound [illustration of uracil's structure], which I will arbitrarily endow with the name "uracil".)
- Alberto Ascoli (1900) "Ueber ein neues Spaltungsprodukt des Hefenucleins" (On a new cleavage product of nucleic acid from yeast), Zeitschrift für Physiologische Chemie, 31 : 161-164.
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- "A Novel Method of Caffeine Synthesis from Uracil". Synthetic Communications 33 (19): 3291–3297. 2003. doi:10.1081/SCC-120023986.
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