Glycolaldehyde
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Glycolaldehyde
Glycolaldehyde is the organic compound with the formula . It is the smallest possible molecule that contains both an aldehyde group () and a hydroxyl group (). It is a highly reactive molecule that occurs both in the biosphere and in the interstellar medium. It is normally supplied as a white solid. Although it conforms to the general formula for carbohydrates, , it is not generally considered to be a saccharide. Structure Glycolaldehyde as a gas is a simple monomeric structure. As a solid and molten liquid, it exists as a dimer. Collins and George reported the equilibrium of glycolaldehyde in water by using NMR. In aqueous solution, it exists as a mixture of at least four species, which rapidly interconvert. In acidic or basic solution, the compound undergoes reversible tautomerization to form 1,2-dihydroxyethene. It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide. While not a true sugar, it is the simplest sugar-relate ...
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Diose
A diose is a monosaccharide containing two carbon atoms. Because the general chemical formula of an unmodified monosaccharide is (C·H2O)''n'', where ''n'' is three or greater, it does not meet the formal definition of a monosaccharide. However, since it does fit the formula (C·H2O)''n'', it is sometimes thought of as the most basic sugar. There is only one possible diose, glycolaldehyde (2-hydroxyethanal), which is an aldodiose (a ketodiose is not possible since there are only two carbons). See also * Triose * Tetrose * Pentose * Hexose * Heptose A heptose is a monosaccharide with seven carbon atoms. They have either an aldehyde functional group in position 1 (aldoheptoses) or a ketone functional group in position 2, 3 or 4 (ketoheptoses). Ketoheptoses have 4 chiral centers, whereas aldoh ... References * Monosaccharides {{biochem-stub ...
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3-Hydroxybutanal
3-Hydroxybutanal (acetaldol) is an organic compound with the formula CH3CH(OH)CH2CHO. It is classified as an aldol, formally the product of the dimerization of acetaldehyde. A colorless liquid, it is a versatile and valuable intermediate with diverse impacts. The compound is chiral although this aspect is not often exploited. Production Acetaldehyde dimerizes upon treatment with aqueous sodium hydroxide: :2CH3CHO → CH3CH(OH)CH2CHO + H2O Reactions and uses Dehydration of 3-hydroxybutanal gives crotonaldehyde. Distillation of 3-hydroxybutanal is sufficiently forcing to effect this conversion: :CH3CH(OH)CH2CHO → CH3CH=CHCHO + H2O Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol: :CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH This diol is a precursor to 1,3-butadiene, precursor to diverse polymers. Polymerization of 3-hydroxybutanal is also spontaneous, but can be stopped with the addition of water. Former or niche uses It was formerly used in medicine as a hypno ...
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5-hydroxyisouric Acid
5-Hydroxyisourate is a molecule with a formula of C5H4N4O4 and molecular weight of 184.110 g/mol. It is the product of the oxidation of uric acid by urate oxidase. References See also * Urate oxidase * Glycolaldehyde Glycolaldehyde is the organic compound with the formula . It is the smallest possible molecule that contains both an aldehyde group () and a hydroxyl group (). It is a highly reactive molecule that occurs both in the biosphere and in the inters ... {{Organic-compound-stub Purines ...
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Lactaldehyde
Lactaldehyde is an intermediate in the methylglyoxal metabolic pathway. Methylglyoxal is converted to D-lactaldehyde by glycerol dehydrogenase (gldA). Lactaldehyde is then oxidized to lactic acid by aldehyde dehydrogenase. Structure Lactaldehyde is a three-carbon atom species with a carbonyl group on the first carbon atom (making it an aldehyde), and a hydroxy group on the second carbon atom, making it a secondary alcohol. The molecule is chiral, its stereocenter being located on the second carbon atom. Lactaldehyde exists in several forms: in open-chain form and as cyclic hemiacetal; in solution and in crystal forms; as monomer and as dimer. In crystal form, three conformers occur as hemiacetal dimers with a 1,4-dioxane 1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers ( 1,2- ... rin ...
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Aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The C=O bond length is about 120-122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors. Al ...
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Allantoic Acid
Allantoic acid is an organic compound with the chemical formula C4H8N4O4. It is a crystalline acid obtained by hydrolysis of allantoin. In nature, allantoic acid is produced from allantoin by the enzyme allantoinase (encoded by the gene AllB (UniprotP77671 in ''Escherichia coli'' and other bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...). References Ureas Acetic acids {{organic-compound-stub ...
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Allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which itself is a degradation product of nucleic acids, by action of urate oxidase (uricase). The occurs as a natural mineral compound ( IMA symbol Aan). History Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemist Louis Nicolas Vauquelin, who mistakenly believed it to be present in the amniotic fluid. In 1821, the French chemist Jean Louis Lassaigne found it in the fluid of the allantois; he called it ''"l'acide allantoique"''. In 1837, the German chemists Friedrich Wöhler and Justus Liebig synthesized it from uric acid and renamed it "allantoïn". Animals Named after the allantois (an amniote embryonic excretory organ in whic ...
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Uric Acid
Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the metabolic breakdown of purine nucleotides, and it is a normal component of urine. High blood concentrations of uric acid can lead to gout and are associated with other medical conditions, including diabetes and the formation of ammonium acid urate kidney stones. Chemistry Uric acid was first isolated from kidney stones in 1776 by Swedish chemist Carl Wilhelm Scheele. In 1882, the Ukrainian chemist Ivan Horbaczewski first synthesized uric acid by melting urea with glycine. Uric acid displays lactam–lactim tautomerism (also often described as keto–enol tautomerism). Although the lactim form is expected to possess some degree of aromaticity, uric acid crystallizes in the lactam form, with computational chemistry also indicating that tautomer to be the most s ...
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Hydrogen Peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%–6% by weight) in water for consumer use, and in higher concentrations for industrial use. Concentrated hydrogen peroxide, or " high-test peroxide", decomposes explosively when heated and has been used as a propellant in rocketry. Hydrogen peroxide is a reactive oxygen species and the simplest peroxide, a compound having an oxygen–oxygen single bond. It decomposes slowly when exposed to light, and rapidly in the presence of organic or reactive compounds. It is typically stored with a stabilizer in a weakly acidic solution in a dark bottle to block light. Hydrogen peroxide is found in biological systems including the human body. Enzymes that use or decompose hydrogen peroxide are classified as peroxidases. Properties The boiling poi ...
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Purine Metabolism
Purine metabolism refers to the metabolic pathways to synthesize and break down purines that are present in many organisms. Biosynthesis Purines are biologically synthesized as nucleotides and in particular as ribotides, i.e. bases attached to ribose 5-phosphate. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which is the first compound in the pathway to have a completely formed purine ring system. IMP Inosine monophosphate is synthesized on a pre-existing ribose-phosphate through a complex pathway (as shown in the figure on the right). The source of the carbon and nitrogen atoms of the purine ring, 5 and 4 respectively, come from multiple sources. The amino acid glycine contributes all its carbon (2) and nitrogen (1) atoms, with additional nitrogen atoms from glutamine (2) and aspartic acid (1), and additional carbon atoms from formyl groups (2), which are transferred from the coenzyme tetrahydrofolate as 10-formyltetrahydrofolate, and a ...
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Pentose Phosphate Shunt
The pentose phosphate pathway (also called the phosphogluconate pathway and the hexose monophosphate shunt and the HMP Shunt) is a metabolic pathway parallel to glycolysis. It generates Nicotinamide adenine dinucleotide phosphate, NADPH and pentoses (5-carbon sugars) as well as ribose 5-phosphate, a precursor for the synthesis of nucleotides. While the pentose phosphate pathway does involve oxidation of glucose, its primary role is anabolism, anabolic rather than catabolism, catabolic. The pathway is especially important in red blood cells (erythrocytes). There are two distinct phases in the pathway. The first is the oxidation, oxidative phase, in which NADPH is generated, and the second is the non-oxidative Chemical synthesis, synthesis of 5-carbon sugars. For most organisms, the pentose phosphate pathway takes place in the cytosol; in plants, most steps take place in plastid, plastids. Like glycolysis, the pentose phosphate pathway appears to have a very ancient evolutionary or ...
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Thiamine Pyrophosphate
Thiamine pyrophosphate (TPP or ThPP), or thiamine diphosphate (ThDP), or cocarboxylase is a thiamine (vitamin B1) derivative which is produced by the enzyme thiamine diphosphokinase. Thiamine pyrophosphate is a cofactor that is present in all living systems, in which it catalyzes several biochemical reactions. Thiamine pyrophosphate is synthesized in the cytosol and is required in the cytosol for the activity of transketolase and in the mitochondria for the activity of pyruvate-, oxoglutarate- and branched chain keto acid dehydrogenases. To date, the yeast ThPP carrier (Tpc1p) the human Tpc and the ''Drosophila melanogaster'' have been identified as being responsible for the mitochondrial transport of ThPP and ThMP. It was first discovered as an essential nutrient (vitamin) in humans through its link with the peripheral nervous system disease beriberi, which results from a deficiency of thiamine in the diet. TPP works as a coenzyme in many enzymatic reactions, such as: * Pyruvat ...
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