1,4-Diaminobutane
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1,4-Diaminobutane
Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors. Production Putrescine is produced on an industrial scale by the hydrogenation of succinonitrile. Biotechnological production of putrescine from renewable feedstock has been investigated. A metabolically engineered strain of '' Escherichia coli'' that produces putrescine at high concentrations in glucose mineral salts medium has been described. Biochemistry Spermidine synthase uses putrescine and ''S''-adenosylmethioninamine (decarboxylated ''S''-adenosyl methionine) to produce spermidine. Spermidine in turn is combined with another ''S''-adenosylmethioninamine and gets converted to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of or ...
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Skeletal Formula
The skeletal formula, or line-angle formula or shorthand formula, of an organic compound is a type of molecular structural formula that serves as a shorthand representation of a molecule's bonding and some details of its molecular geometry. A skeletal formula shows the skeletal structure or skeleton of a molecule, which is composed of the skeletal atoms that make up the molecule. It is represented in two dimensions, as on a piece of paper. It employs certain conventions to represent carbon and hydrogen atoms, which are the most common in organic chemistry. An early form of this representation was first developed by organic chemist August Kekulé, while the modern form is closely related to and influenced by the Lewis structure of molecules and their valence electrons. Hence they are sometimes termed Kekulé structures or Lewis–Kekulé structures. Skeletal formulae have become ubiquitous in organic chemistry, partly because they are relatively quick and simple to draw, and ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Ornithine Decarboxylase
The enzyme ornithine decarboxylase (, ODC) catalyzes the decarboxylation of ornithine (a product of the urea cycle) to form putrescine. This reaction is the committed step in polyamine synthesis. In humans, this protein has 461 amino acids and forms a homodimer. Reaction mechanism Lysine 69 on ornithine decarboxylase (ODC) binds the cofactor pyridoxal phosphate to form a Schiff base. Ornithine displaces the lysine to form a Schiff base attached to orthonine, which decarboxylates to form a quinoid intermediate. This intermediate rearranges to form a Schiff base attached to putrescine, which is attacked by lysine to release putrescine product and reform PLP-bound ODC. This is the first step and the rate-limiting step in humans for the production of polyamines, compounds required for cell division. Structure image:Ornithine Decarboxylase Publication View.png, 270px, 3D crystal structure of ornithine decarboxylase.; ; rendered viPyMOL The active form of ornithine decarboxyla ...
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Spermine
Spermine is a polyamine involved in cellular metabolism that is found in all Eukaryote, eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some Bacterium, bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses. Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678. The name ''spermin'' was first used by the German chemists Albert Ladenburg, Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.). Spermine is the chemical primarily responsible for the characteristic odor of semen. Derivative A derivative (chemistry), derivative of spermine, N1, N12-bis(ethyl)spermine (also known as BESm) was investig ...
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Spermidine
Spermidine is a polyamine compound () found in ribosomes and living tissues and having various metabolic functions within organisms. It was originally isolated from semen. Function Spermidine is an aliphatic polyamine. Spermidine synthase (SPDS) catalyzes its formation from putrescine. It is a precursor to other polyamines, such as spermine and its structural isomer thermospermine. Spermidine synchronizes an array of biological processes, (such as Ca2+, Na+, K+ -ATPase) thus maintaining membrane potential and controlling intracellular pH and volume. Spermidine regulates biological processes, such as Ca2+ influx by glutamatergic N-methyl-d-aspartate receptor (NMDA receptor), which has been associated with nitric oxide synthase (NOS) and cGMP/PKG pathway activation and a decrease of Na+,K+-ATPase activity in cerebral cortex synaptosomes. Spermidine is a longevity agent in mammals due to various mechanisms of action, which are just beginning to be understood. Autophagy is the main m ...
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S-Adenosyl Methionine
''S''-Adenosyl methionine (SAM), also known under the commercial names of SAMe, SAM-e, or AdoMet, is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM is produced and consumed in the liver. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase. SAM was first discovered by Giulio Cantoni in 1952. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation; immune response; amino acid metabolism; transsulfuration; and more. In plants, SAM is crucial to the biosynthesis of ethylene, an important plant hormone and sig ...
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S-Adenosylmethioninamine
''S''-Adenosylmethioninamine is a substrate that is required for the biosynthesis of polyamines including spermidine, spermine, and thermospermine. It is produced by decarboxylation of ''S''-adenosyl methionine. See also * Adenosylmethionine decarboxylase * Spermidine synthase * Spermine synthase Spermine synthase (, ''spermidine aminopropyltransferase'', ''spermine synthetase'') is an enzyme that converts spermidine into spermine. This enzyme catalyses the following chemical reaction : S-adenosylmethioninamine + spermidine \rightlefthar ... * Thermospermine synthase (ACAULIS5) References Nucleosides Purines Organosulfur compounds Cations {{biochem-stub ...
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Spermidine Synthase
Spermidine synthase is an enzyme () that catalyzes the transfer of the propylamine group from ''S''-adenosylmethioninamine to putrescine in the biosynthesis of spermidine. The systematic name is S-adenosyl 3-(methylthio)propylamine:putrescine 3-aminopropyltransferase and it belongs to the group of aminopropyl transferases. It does not need any cofactors. Most spermidine synthases exist in solution as dimers. Specificity With exception of the spermidine synthases from ''Thermotoga maritimum'' and from ''Escherichia coli'', which accept different kinds of polyamines, all enzymes are highly specific for putrescine. No known spermidine synthase can use ''S''-adenosyl methionine. This is prevented by a conserved aspartatyl residue in the active site, which is thought to repel the carboxyl moiety of ''S''-adenosyl methionine. The putrescine-N-methyl transferase whose substrates are putrescine and ''S''-adenosyl methionine and which is evolutionary related to the spermidine synthase ...
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Polyamine Synthesis
A polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. Most aromatic polyamines are crystalline solids at room temperature. Natural polyamines Low-molecular-weight linear polyamines are found in all forms of life. The principal examples are the triamine spermidine and the tetraamine spermine. They are structurally and biosynthetically related to the diamines putrescine and cadaverine. Polyamine metabolism is regulated by the activity of the enzyme ornithine decarboxylase (ODC). Polyamines are found in high concentrations in the mammalian brain. File:Spermidine-2D-skeletal.svg, spermidine File:Spermine.svg, spermine Synthetic polyamines Several synthetic polyamines are used in chemical industry and the research laboratory. They are mainly of interest as additives to motor oil and as co-rea ...
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Escherichia Coli
''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escherichia'' that is commonly found in the lower intestine of warm-blooded organisms. Most ''E. coli'' strains are harmless, but some serotypes ( EPEC, ETEC etc.) can cause serious food poisoning in their hosts, and are occasionally responsible for food contamination incidents that prompt product recalls. Most strains do not cause disease in humans and are part of the normal microbiota of the gut; such strains are harmless or even beneficial to humans (although these strains tend to be less studied than the pathogenic ones). For example, some strains of ''E. coli'' benefit their hosts by producing vitamin K2 or by preventing the colonization of the intestine by pathogenic bacteria. These mutually beneficial relationships between ''E. col ...
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Succinonitrile
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C. Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation): :CH2=CHCN + HCN → NCCH2CH2CN Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane). See also * Malononitrile - A di-nitrile with 3 carbon atoms * Glutaronitrile - A di-nitrile with 5 carbon atoms * Adiponitrile Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adip ... - A di-nitrile with 6 carbon atoms References External links WebBook page for C4H4N2 Alkanedinitriles {{Organic-compound-stub ...
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Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated and unsaturated compounds, saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces Double bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same ca ...
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