Uracil

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Uracil

Uracil is a common and naturally occurring pyrimidine

Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
derivative. Originally discovered in 1900, it was isolated by hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
of yeast

Yeast

Yeasts are eukaryote microorganisms classified in the Kingdom fungus, with about 1,500 species currently described; they dominate fungal diversity in the oceans....
nuclein that was found in bovine thymus

Thymus

In human anatomy, the thymus is an organ located in the upper anterior portion of the Thoracic cavity just behind the sternum. The main function of the thymus is to provide an area for T lymphocyte maturation....
and spleen

Spleen

The spleen is an organ found in all vertebrate animals. In humans, the spleen is located in the abdomen of the body, where it functions in the destruction of redundant red blood cells, and holds a reservoir of blood....
, herring

Herring

Herring are small, oily fish of the genus Clupea found in the shallow, temperate waters of the North Pacific Ocean and the North Atlantic Ocean, including the Baltic Sea....
, sperm

Sperm

The term sperm is derived from the Greek word sperma and refers to the male reproductive Cell . In the types of sexual reproduction known as anisogamy and oogamy, there is a marked difference in the size of the gametes with the smaller one being termed the "male" or sperm cell....
, and wheat

Wheat

Wheat , is a worldwide cultivated Poaceae from the Levant region of the Middle East. Globally, after maize, wheat is the second most-produced food among the cereal just above rice....
germ

Germ

germ can mean:* Microorganism, especially a pathogen; see Germ theory of disease* germ, a cell that has all the information to grow into a complete adult organism...
. It is a planar, unsaturated compound that has the ability to absorb light.

d in RNA

RNA

Ribonucleic acid is a type of molecule that consists of a long chain of nucleotide units. Each nucleotide consists of a nucleobase, a ribose sugar, and a phosphate....
, it base pair

Base pair

In molecular biology, two nucleotides on opposite complementarity DNA or RNA strands that are connected via hydrogen bonds are called a base pair ....
s with adenine

Adenine

Thymine

Thymine is one of the four bases in the nucleic acid of DNA that make up the letters GCAT. The others are adenine, guanine, and cytosine. Thymine always pairs with adenine....
in DNA

DNA

Deoxyribonucleic acid is a nucleic acid that contains the genetics instructions used in the development and functioning of all known living organisms and some viruses....
. Methylation of uracil produces thymine

Thymine

Thymine is one of the four bases in the nucleic acid of DNA that make up the letters GCAT. The others are adenine, guanine, and cytosine. Thymine always pairs with adenine....
. It turns into thymine to protect the DNA and to improve the efficiency of DNA replication

DNA replication

DNA replication, the basis for heredity, is a fundamental process occurring in all living organisms to copy their DNA. This process is "semiconservative replication" in that each strand of the original double-stranded DNA molecule serves as template for the reproduction of the complementary strand....
.

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Properties

Found in RNA

RNA

Ribonucleic acid is a type of molecule that consists of a long chain of nucleotide units. Each nucleotide consists of a nucleobase, a ribose sugar, and a phosphate....
, it base pair

Base pair

In molecular biology, two nucleotides on opposite complementarity DNA or RNA strands that are connected via hydrogen bonds are called a base pair ....
s with adenine

Adenine

Thymine

Thymine is one of the four bases in the nucleic acid of DNA that make up the letters GCAT. The others are adenine, guanine, and cytosine. Thymine always pairs with adenine....
in DNA

DNA

Thymine

DNA replication

Helix

A helix is a special kind of space curve, i.e. a Differentiable manifold curve in three-space. As a mental image of a helix one may take the spring ....
, but readily pairs with adenine

Adenine

Adenine is a nucleobase with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate and the cofactor s nicotinamide adenine dinucleotide and flavin adenine dinucleotide , and Protein biosynthesis, as a chemical component of DNA and RNA....
because the methyl group is repelled into a fixed position. Uracil pairs with adenine through hydrogen bonding. Uracil is the hydrogen bond acceptor and can form two hydrogen bonds. Uracil can also bind with a ribose

Ribose

Ribose, primarily occurring as D-ribose, is an organic compound that occurs widely in nature. It is an aldopentose, that is a monosaccharide containing five carbon atoms that, in its acyclic form, has an aldehyde functional group at one end....
sugar to form a ribonucleoside

Ribonucleoside

A ribonucleoside is a type of nucleoside including ribose as a component.An example is cytidine.References...
, uridine

Uridine

Uridine is a molecule that is formed when uracil is attached to a ribose ring via a ?-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
. When a phosphate

Phosphate

A phosphate, an inorganic chemical, is a Salt of phosphoric acid. Inorganic phosphates are mining to obtain phosphorus for use in agriculture and industry....
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

Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
is compensated by the cyclic-amidic stability. The keto tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. Commonly this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond....
is referred to the lactam

Lactam

A lactam is a simple aromatic ring amide. Prefixes indicate how many carbon atoms are present in the ring: beta-lactam , ?-lactam , d-lactam ....
structure, while the imidic acid tautomer is referred to as the lactim

Lactim

Lactim is a cyclic carboximidic acid compound characterized by an endocyclic carbon-nitrogen double bond. It is tautomerism with lactam....
structure. These tautomeric forms are predominant at pH

pH is a measure of the Acid or Base of a solution. It is defined as the cologarithm of the Activity of dissolved hydrogen ions . Hydrogen ion activity coefficients cannot be measured experimentally, so they are based on theoretical calculations....
=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 substrates, aspartate, carbon dioxide

Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
, and ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
.

C₄H₄N₂O₂ ? H₃NCH₂CH₂COO^- + NH₄ + CO₂

Oxidative degradation of uracil produces urea and maleic acid in the presence of H₂O₂

Hydrogen peroxide

Hydrogen peroxide is a very pale blue liquid which appears colorless in a dilute solution, slightly more viscous than water. It is a weak acid....
and Fe

Fe may refer to:*Fantasy Empires, a 1993 Dungeons & Dragons computer game*Fast Ethernet*Fe , The debut album by Souled American*Fe , the f-rune, of the Younger Futhark...
²⁺ or in the presence of diatomic oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
and Fe²⁺.

Uracil is a weak acid

Weak acid

A weak acid is an acid that dissociates incompletely and does not release all of its hydrogens in a solution i.e it does not completely donate all of its protons....
, the first site of ionization

Ionization

Ionization is the physics process of converting an atom or molecule into an ion by adding or removing charged particles such as electrons or other ions....
of uracil is not known. The negative charge is placed on the oxygen anion and produces a pK_a

Acid dissociation constant

An acid dissociation constant, Ka, is a quantitative measure of the strong acid in solution. It is the equilibrium constant for a chemical reaction known as Dissociation in the context of acid-base reactions....
of less than or equal to 12. The basic pK_a = -3.4, while the acidic pK_a = 9.38_{9. In the gas phase, uracil has 4 sites that are more acidic than water.

Synthesis
There are many laboratory synthesesChemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
of uracil available. The first reaction is the simplest of the syntheses, by adding water to cytosineCytosine

Cytosine is one of the five main bases found in DNA and RNA. It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached ....
to produce uracil and ammoniaAmmonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
. The most common way to synthesize uracil is by the condensationCondensation

Condensation is the change of the physical state of aggregation of matter from gaseous phase into liquid phase. When the transition happens from the gaseous phase into the solid phase directly, bypassing the liquid phase the change is called Deposition , which is the opposite of sublimation....
of malic acidMalic acid

Malic acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods....
with urea in fuming sulfuric acid as seen below also. Uracil can also be synthesized by a double decomposition of thiouracilThiouracil

Thiouracil refers both to a specific molecule consisting of a sulfated uracil, and a family of molecules based upon that structure. The substance is a historically relevant antithyroid preparation; Astwood E.B....
in aqueous chloroacetic acidChloroacetic acid

Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis....
.

C₄H₅N₃O + H₂O ? C₄H₄N₂O₂ + NH₃

C₄H₄O₄ + CH₄N₂O ? C₄H₄N₂O₂ + 2 H₂O + CO

Photodehydrogenation of 5,6-diuracil, which is synthesized by beta-alanineAlanine

Alanine is an a-amino acid with the chemical formula CH3CHCOOH. The L-isomer is one of the 20 proteinogenic amino acids, i.e. the building blocks of proteins....
reacting with ureaUrea

Urea is an organic compound with the chemical formula 2carbonoxygen.Urea is also known by the International Nonproprietary Name carbamide, as established by the World Health Organization....
, produces uracil.

Reactions
Uracil readily undergoes regular reactions including oxidation, nitrationNitration

Nitration is a general chemical process for the introduction of a nitro compound into a chemical compound. Examples of nitrations are the conversion of glycerin to nitroglycerin and the conversion of toluene to trinitrotoluene....
, and alkylationAlkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
. While in the presence of PhOHPhenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
/NaOClSodium hypochlorite

Sodium hypochlorite is a chemical compound with the chemical formula NaClO. Sodium hypochlorite solution, commonly known as bleach, is frequently used as a disinfectant or a bleaching agent....
, uracil can be visualized in the blue region of UV light. Uracil also has the capability to react with elemental halogenHalogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
s because of the presence of more than one strongly electron donating group.

Uracil readily undergoes addition to riboseRibose

Ribose, primarily occurring as D-ribose, is an organic compound that occurs widely in nature. It is an aldopentose, that is a monosaccharide containing five carbon atoms that, in its acyclic form, has an aldehyde functional group at one end....
sugarSugar

Sugar is a class of edible crystalline substances, mainly sucrose, lactose, and fructose. Human taste buds interpret its flavor as sweet. Sugar as a basic food carbohydrate primarily comes from sugar cane and from sugar beet, but also appears in fruit, honey, sorghum, sugar maple , and in many other sources....
s and phosphatePhosphate

A phosphate, an inorganic chemical, is a Salt of phosphoric acid. Inorganic phosphates are mining to obtain phosphorus for use in agriculture and industry....
s to partake in synthesis and further reactions in the body. Uracil becomes uridineUridine

Uridine is a molecule that is formed when uracil is attached to a ribose ring via a ?-N1-glycosidic bond.If uracil is attached to a deoxyribose ring, it is known as a deoxyuridine....
, uridine monophosphateUridine monophosphate

Uridine monophosphate, also known as 5'-uridylic acid and abbreviated UMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine....
(UMP), uridine diphosphateUridine diphosphate

Uridine diphosphate, abbreviated UDP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleoside uridine. UDP consists of the pyrophosphate Functional group, the pentose sugar ribose, and the nucleobase uracil....
(UDP), uridine triphosphate (UTP), and uridine diphosphate glucoseUridine diphosphate glucose

Uridine diphosphate glucose is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism....
(UDP-glucose). Each one of these molecules in synthesized in the body and has specific functions.

When uracil reactes with anhydrous hydrazineHydrazine

Hydrazine is a chemical compound with the chemical formula N2H4. It is a colourless liquid with an ammonia-like odor and is derived from the same industrial chemistry processes that manufacture ammonia....
a first order kinetic reaction occurs and the ring of uracil opens up. If the pH of the reaction increases to >10.5 the uracil anion forms making the reaction go much slower, the same slowing of the reaction occurs if the pH decreases because of the protonation of the hydrazine. The reactivity of uracil is unchanged even if the temperature changes.

Uses
Uracil can be used for drug deliveryDrug delivery

Drug delivery is the method or process of administering a pharmaceutical compound to achieve a therapeutic effect in humans or animals . Drug Delivery technologies are patent protected formulation technologies that modifies drug release profile, absorption, distribution and elimination for the benefit of improving product efficacy & safety a...
and as a pharmaceutical. When elemental fluorineFluorine

Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....
is reacted with uracil, 5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetaboliteAntimetabolite

An antimetabolite is a chemical that enzyme inhibition the use of a metabolite, which is another chemical that is part of normal metabolism. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolates that interfere with the use of folic acid....
) used to masqueradeMasquerade

Masquerade or Masqueraders may refer to:...
as uracil during the nucleic acid replication process. Because 5-Fluorouracil is similar in shape to, but does not perform the same chemistry as uracil the drug inhibits RNARNA

Ribonucleic acid is a type of molecule that consists of a long chain of nucleotide units. Each nucleotide consists of a nucleobase, a ribose sugar, and a phosphate....
replication enzymes, thereby eliminating RNA synthesis and stopping the growth of cancerous cells.

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 coenzymeCoenzyme

Many enzymes require a cofactor for catalytic activity, accelerating the transformation of a specific substrate to a particular product. The inactive protein, without the cofactor is called an apoenzyme, while the complete enzyme with cofactor is the holoenzyme....
for reactions in the human body and in plants. UMP controls the activity of carbamoyl phosphate synthetaseCarbamoyl phosphate synthetase

Carbamoyl phosphate synthetase is an enzyme that catalyzes a reaction that produces carbamoyl phosphate. This enzyme catalyzes the reaction of Adenosine triphosphate and bicarbonate to produce carbonyl phosphate and ADP....
and aspartate transcarbamoylase in plants, while UDP and UTP requlate CPSase II activity in animalAnimal

Animals are a major group of multicellular, eukaryotic organisms of the Kingdom Animalia or Metazoa. Their body plan eventually becomes fixed as they develop, although some undergo a process of metamorphosis later on in their life....
s. UDP-glucose regulates the conversion of glucoseGlucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
to galactoseGalactose

Galactose is a type of Carbohydrate which is less sweetness than glucose. It is considered a nutritive sweetener because it has food energy.Galactan is a polymer of the sugar galactose....
in the liverLiver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
and other tissues in the process of carbohydrate metabolismCarbohydrate metabolism

Carbohydrate metabolism denotes the various biochemistry processes responsible for the anabolism, catabolism and interconversion of carbohydrates in life organisms....
. Uracil is also involved in the biosynthesisBiosynthesis

Biosynthesis is a phenomenon wherein chemical compounds are produced from simpler reagents. Biosynthesis, unlike chemosynthesis, takes place within living organisms and is generally catalyst by enzymes....
of polysaccharides and the transportation of sugars containing aldehydes.

It can also increase the risk for cancer in cases where 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 to determine microbial contamination of tomatoTomato

The Tomato is an herbaceous, usually sprawling plant in the Solanaceae or nightshade family, as are its close cousins Nicotiana, potatoes, aubergine , chilli peppers, and the poisonous Atropa belladonna....
es. The presence of uracil is an indication of lactic acidLactic acid

Lactic acid , also known as milk acid, is a chemical compound that plays a role in several biochemistry processes. It was first isolated in 1780 by a Swedish chemist, Carl Wilhelm Scheele, and is a carboxylic acid with a chemical formula of C3H6O3....
bacteriaBacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
contamination in the fruit. Uracil derivatives containing a diazineDiazine

Diazine refers to a group of organic compounds having the molecular formula C4H4N2. Each contains a benzene ring in which two of the C-H fragments have been replaced by isolobal nitrogen....
ring are used in pesticides. Uracil derivatives are more often used as antiphotosynthetic herbicides, destroying weeds in cottonCotton

Cotton is a soft, staple fiber that grows in a form known as a boll around the seeds of the cotton plant a shrub native to tropical and subtropical regions around the world, including the Americas, India and Africa....
, sugar beetSugar beet

Sugar beet , a member of the Chenopodiaceae family, is a plant whose root contains a high concentration of sucrose. It is grown commercially for sugar production....
, turnips, soyaSoybean

The soybean or soya bean is a species of legume native to East Asia. The plant is classed as an oilseed rather than a Pulse . It is an annual plant that has been used in China for 5,000 years as a food and a component of drugs....
, peasPEAS

P.E.A.S. is an acronym in artificial intelligence that stands for Performance, Environment, Actuators, Sensors....
, sunflowerSunflower

The sunflower is an annual plant in the family Asteraceae and native to the Americas, with a large flowering head . The stem can grow as high as 3 meters , and the flower head can reach 30 cm in diameter with the "large" seeds....
crops, vineyards, berryBerry

In everyday English, a berry is a broad term for any small edible fruit. Most berries are juicy, round or semi-oblong, brightly coloured, sweet or sour, and don't have a stone or pit....
plantations, and orchards.}