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Spermine
Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some 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. It functions as an intracellular free radical scavenger to protect DNA from free radical attack. Spermine is the chemical primarily responsible for the characteristic odor of semen. Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678. The name ''spermin'' was first used by the German chemists 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.). Derivative A derivative of spermine, N1, N12-bis(ethyl)sperm ...
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Polyamine
A polyamine is an organic compound having two or more 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 Ethyleneamines are a commercially-important class of synthetic polyamines with ethylene ( linkages); global production capacity was estimated at 385,00 ...
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Polyamine Synthesis
A polyamine is an organic compound having two or more 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 Ethyleneamines are a commercially-important class of synthetic polyamines with ethylene ( linkages); global production capacity was estimated at 385,000 t ...
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Spermidine
Spermidine is a polyamine compound () found in ribosomes and living tissues and having various metabolic functions within organisms. Function Spermidine is an Aliphatic compound, aliphatic polyamine. Spermidine synthase (SPDS) catalyzes its formation from putrescine. It is a precursor to other polyamines, such as spermine and its structural isomer polyamine#thermospermine, 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-aspartic acid, ''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 ...
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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 (AMD1) * 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 \rightleftha ... * 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 syntha ...
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Spermidine
Spermidine is a polyamine compound () found in ribosomes and living tissues and having various metabolic functions within organisms. Function Spermidine is an Aliphatic compound, aliphatic polyamine. Spermidine synthase (SPDS) catalyzes its formation from putrescine. It is a precursor to other polyamines, such as spermine and its structural isomer polyamine#thermospermine, 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-aspartic acid, ''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 ...
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Cellular Metabolism
Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the conversion of food to building blocks of proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of metabolic wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their structures, and respond to their environments. The word ''metabolism'' can also refer to the sum of all chemical reactions that occur in living organisms, including digestion and the transportation of substances into and between different cells, in which case the above described set of reactions within the cells is called intermediary (or intermediate) metabolism. Metabolic reactions may be categorized as ''catabolic''—the ''breaking down'' of compounds (for example, of glucose to pyruvate by cellular respiration); o ...
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Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction. In the past, derivative also meant a compound that ''can be imagined to'' arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms, but modern chemical language now uses the term structural analog for this meaning, thus eliminating ambiguity. The term "structural analogue" is common in organic chemistry. In biochemistry, the word is used for compounds that at least theoretically can be formed from the precursor compound. Chemical derivatives may be used to facilitate analysis. For example, melting point (MP) analysis can assist in identification of many organic compounds. A crystalline derivative may be prepared, such as a semicarbazone or 2,4-dinitrophenylhydrazone (derived from aldehydes or ketones), as a simple way of verifying the identity of the original compound, assuming that a table of derivative MP values is avai ...
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Cadaverine
Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of Tissue (biology)#Animal tissue, animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors. Production Cadaverine is produced by decarboxylation of lysine.Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane. History Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). It was named from the English adjective ''cadaverous''. Receptors In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified a ...
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Diethylenetriamine
Diethylenetriamine (abbreviated and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride. Reactions and uses Diethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets. It is N-alkylated upon reaction with epoxide groups forming crosslinks. In coordination chemistry, it serves as a tridentate ligand forming complexes such as Co(dien)(NO2)3. Like some related amines, it is used in oil industry for the extraction of acid gas. Like ethylenediamine, DETA can also be used to sensitize nitromethane, mak ...
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