Pyrimidines
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Pyrimidines
Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine (nitrogen atoms at the 1 and 4 positions) and pyridazine (nitrogen atoms at the 1 and 2 positions). In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U). Occurrence and history The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. It is also found in many synthetic compounds such as barbiturates and the HIV drug zidovudine. Although pyrimidine derivatives such as alloxan were known in the early 19th century, a laboratory synthesis of a pyrimidine was not carried out until 1879, when Grimaux reported the ...
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Nucleotides
Nucleotides are Organic compound, organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both of which are essential biomolecules within all Life, life-forms on Earth. Nucleotides are obtained in the diet and are also synthesized from common Nutrient, nutrients by the liver. Nucleotides are composed of three subunit molecules: a nucleobase, a pentose, five-carbon sugar (ribose or deoxyribose), and a phosphate group consisting of one to three phosphates. The four nucleobases in DNA are guanine, adenine, cytosine, and thymine; in RNA, uracil is used in place of thymine. Nucleotides also play a central role in metabolism at a fundamental, cellular level. They provide chemical energy—in the form of the nucleoside triphosphates, adenosine triphosphate (ATP), guanosine triphosphate (GTP), cytidine triphosphate (CTP), and uridine triph ...
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Thiamine
Thiamine, also known as thiamin and vitamin B1, is a vitamin – an Nutrient#Micronutrients, essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some Metabolism, metabolic reactions, including the breakdown of Carbohydrate metabolism, glucose and amino acids. Food sources of thiamine include whole grains, legumes, and some meats and fish. Refined grain, Grain processing removes much of the vitamin content, so in many countries cereals and flours are food fortification, enriched with thiamine. Supplements and medications are available to treat and prevent thiamine deficiency and the disorders that result from it such as Thiamine deficiency#Dry beriberi, beriberi and Wernicke encephalopathy. They are also used to treat maple syrup urine disease and Leigh syndrome. Supplements and medications are typically taken Route of administration#Oral ...
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Uracil
Uracil () (nucleoside#List of nucleosides and corresponding nucleobases, symbol U or Ura) is one of the four nucleotide bases in the nucleic acid RNA. 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 (T). Uracil is 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 Cereal germ, germ. It is a planar, unsaturated compound that has the ability to absorb light. Uracil that was formed extraterrestrially has been detected in the Murchison meteorite, in near-Earth asteroid 162173 Ryugu, Ryugu, and possibly on the surface of th ...
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Barbituric Acid
Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer. Naming It remains unclear why Baeyer chose to name the compound that he discovered "barbituric acid". In his textbook ''Organic Chemistry'', the American organic chemist Louis Fieser, Louis Frederick Fieser (1899–1977) initially speculated that the name stemmed from the German word ''Schlüsselbart'' (literally, the beard (''Bart'', Latin: ''barba'') of a key (''Schlüssel''), that is, the bit (key), bit of a key), because Baeyer had regarded barbituric acid as central (or "key") to understanding uric acid and its derivatives. However, Fieser subsequently decided that Baeyer had named the compound after a young lady whom he had met and who was ...
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Nucleobases
Nucleotide bases (also nucleobases, nitrogenous bases) are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic building blocks of nucleic acids. The ability of nucleobases to form base pairs and to stack one upon another leads directly to long-chain helical structures such as ribonucleic acid (RNA) and deoxyribonucleic acid (DNA). Five nucleobases—adenine (A), cytosine (C), guanine (G), thymine (T), and uracil (U)—are called ''primary'' or ''canonical''. They function as the fundamental units of the genetic code, with the bases A, G, C, and T being found in DNA while A, G, C, and U are found in RNA. Thymine and uracil are distinguished by merely the presence or absence of a methyl group on the fifth carbon (C5) of these heterocyclic six-membered rings. In addition, some viruses have 2,6-diaminopurine, aminoadenine (Z) instead of adenine. It differs in having an extra ...
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Alloxan
Alloxan, sometimes referred to as alloxan monohydrate, is an organic compound with the formula . It is classified as a derivative of pyrimidine. The anhydrous derivative is also known, as well as a dimeric derivative. These are some of the earliest known organic compounds. They exhibit a variety of biological activities. History and literature The compound was discovered by Justus von Liebig and Friedrich Wöhler. It is one of the oldest named organic compounds. It was originally prepared in 1818 by Luigi Valentino Brugnatelli (1761-1818) and was named in 1838 by Wöhler and Liebig. The name "Alloxan" emerged from an amalgamation of the words " Allantoïn" and "Oxalsäure" (oxalic acid). The alloxan model of diabetes was first described in rabbits by Dunn, Sheehan and McLetchie in 1943. The name is derived from allantoin, a product of uric acid excreted by the fetus into the allantois, and oxaluric acid derived from oxalic acid and urea, found in urine. Alloxan was used i ...
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Chemische Berichte
''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with '' Recueil des Travaux Chimiques des Pays-Bas'' to form ''Chemische Berichte/Recueil'' in 1997. ''Chemische Berichte/Recueil'' was then merged with other European journals in 1998 to form ''European Journal of Inorganic Chemistry''. History Founded in 1868 as ''Berichte der Deutschen Chemischen Gesellschaft'' (, CODEN BDCGAS), it operated under this title until 1928 (Vol. 61). The journal was then split into: * ''Berichte der Deutschen Chemischen Gesellschaft, A: Vereins-Nachrichten'' (, CODEN BDCAAS), and * ''Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen'' (, CODEN BDCBAD). Vol. 78 and 79 (1945–1946) were omitted and not published due to World War II. The journal was renamed ''Chemische Berichte'' (, CODEN CHBEAM) in 1 ...
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Adolf Pinner
Adolf Pinner (August 31, 1842 – May 21, 1909) was a German chemist. Early life and education He was educated at the Jewish Theological Seminary at Breslau and at the University of Berlin (Phd in Chemistry (Doctor der Chemie), 1867). In 1871, he became privat-docent at the University of Berlin. In 1873, he became assistant professor of chemistry at the University of Berlin, and in 1874 professor of chemistry at the veterinary college of that city. In 1884, he was appointed a member of the German patent office, and in the following year, of the technical division of the Prussian Department of Commerce. He has received the title "''Geheimer Regierungsrat''". Literary works Pinner contributed many essays to the professional journals, among which may be mentioned: * "''Darstellung und Untersuchung des Butylchlorals''," in "'' Annalen der Chemie''", clxxix., and in "''Berichte der Deutschen Chemischen Gesellschaft''", 1870–77; * "''Ueber Imidoäther''" in "''Annalen''", ccx ...
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Ethyl Acetoacetate
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. Preparation At large scale, ethyl acetoacetate is industrially produced by treatment of diketene with ethanol. The small scale preparation of ethyl acetoacetate is a classic laboratory procedure. It involves Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol. : Reactions Ethyl acetoacetate is subject to keto-enol tautomerism. In the neat liquid at 33 °C, the enol consists of 8% of the total. The enol is moderately acidic. Thus ethyl acetoacetate behaves similarly to acetylacetone: : The resulting carbanion undergoes nucleophilic substitution. Ethyl acetoacetate is often used in the acetoacetic ester synthesis, comparable to diethyl malonate in the malonic ester synthesis or the Kn ...
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Malonic Acid
Malonic acid is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (''malon'') meaning 'apple'. History Malonic acid is a naturally occurring substance found in many fruits and vegetables. There is a suggestion that citrus fruits produced in organic farming contain higher levels of malonic acid than fruits produced in conventional agriculture. Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid. Hermann Kolbe and Hugo Müller independently discovered how to synthesize malonic acid from propionic acid, and decided to publish their results back-to-back in the Chemical Society journal in 1864. This led to priority dispute with Hans Hübner and Maxwell Simpson who had independently published preliminary results on rela ...
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Amidine
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines include: * 1,8-Diazabicycloundec-7-ene, DBU * diminazene * benzamidine * Pentamidine * Paranyline Preparation A common route to primary amidines is the Pinner reaction. Reaction of the nitrile with alcohol in the presence of acid gives an Carboximidate, iminoether. Treatment of the resulting compound with ammonia then completes the conversion to the amidine. Instead of using a Brønsted–Lowry acid–base theory, Bronsted acid, Lewis acids and bases, Lewis acids such as Aluminium chloride, aluminium trichloride promote the direct amination of nitriles, or, in certain exceptional cases, of amides. Dimethylformamide acetal reacts with primary amines to give amidines: :Me2NC(H)(OMe)2 + RNH2 → Me2NC=NHR + 2 MeOH Catalysis is likewise not require ...
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Urea
Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important role in the cellular metabolism of nitrogen-containing compounds by animals and is the main nitrogen-containing substance in the urine of mammals. ''Urea'' is Neo-Latin, , , itself from Proto-Indo-European ''*h₂worsom''. It is a colorless, odorless solid, highly soluble in water, and practically non-toxic ( is 15 g/kg for rats). Dissolved in water, it is neither acidic nor base (chemistry), alkaline. The body uses it in many processes, most notably metabolic waste#Nitrogen wastes, nitrogen excretion. The liver forms it by combining two ammonia molecules () with a carbon dioxide () molecule in the urea cycle. Urea is widely used in fertilizers as a source of nitrogen (N) and is an important ...
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