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Polyamines
A polyamine is an organic compound having two or more amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, Hygroscopy, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. Most aromatic compound, 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 capac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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. In humans, ornithine decarboxylase (ODC) is expressed by the gene ''ODC1''. The protein ODC is sometimes referred to as "ODC1" in research pertaining to humans and mice, but certain species such as ''Drosophila'' (''dODC2''), species of Solanaceae plant family (''ODC2''), and the lactic acid bacteria '' Paucilactobacillus wasatchensis'' (''odc2'') have been shown to have a second ODC gene. 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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclam
Cyclam (1,4,8,11-tetraazacyclotetradecane) is an organic compound with the formula (NHCH2CH2NHCH2CH2CH2)2. Classified as an aza-crown ether, it is a white solid that is soluble in water. As a macrocyclic ligand, it binds strongly to many transition metal cations. The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine. The compound features four secondary amines. Its complexes therefore can exist as several diastereomers, depending on the relative orientation of the N–H centres. Its complexes feature alternating five- and six-membered chelate rings. The closely related ligand cyclen ((CH2CH2NH)4) forms only five-membered C2N2M chelate rings and tends not to form square-planar complexes. ''N''-Alkyl derivatives Metal-cyclam complexes are prone to oxidative degradation, which is initiated by deprotonation of the secondary amine. This flaw led to the development of cyclam derivatives wherein the NH centres are replaced by tertiary amines. F ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,1,1-Tris(aminomethyl)ethane
1,1,1-Tris(aminomethyl)ethane (TAME) is an organic compound with the formula CHC(CHNH). It is a colorless liquid. It is classified as a polyamine tripodal ligand, i.e., capable of binding to metal ions through three sites and hence is a tridentate chelating ligand, occupying a face of the coordination polyhedron. Preparation TAME is synthesized by the Pd/C-catalyzed hydrogenation of 1,1,1-tris(azidomethyl)ethane. Although azides are potentially explosive, they are excellent and practical source of primary amines. The required tris(azidomethyl)ethane is obtained from the tri tosylate by salt metathesis using sodium azide. These two steps are: :3 NaN + CHC(CHOTs) → CHC(CHN) + 3 NaOTs :3 H + CHC(CHN) → CHC(CHNH) + 3 N Complexes of TAME The tripodal TAME ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyethyleneamine
Ethyleneamines are a class of amine compounds containing ethylene (-CH2CH2-) linkages between amine groups. These compounds are generally colorless, low-viscosity liquids with a fishy amine odor. They are primarily used as building block chemicals and in epoxy resin curing agent chemistry. Production There are two main routes for the production of ethyleneamines, the reaction between ethylene dichloride and ammonia, and the reductive amination of monethanolamine. World capacity of ethyleneamines for the year 2001 was estimated to be 385,000 tonnes/year, with the majority comprising the ethylene dichloride route. In the ethylene dichloride route, the initial product of this reaction is ethylenediamine. In the presence of excess ethylene dichloride, the initial ethyleneamine is extended by one ethylene unit. The terminal alkyl chloride reacts with ammonia to give the amine, and the polyamine chain can be extended further in this fashion. Addition of a polyamine to the initial reac ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclen
Cyclen (1,4,7,10-tetraazacyclododecane) is an aza-crown ether with the formula (CH2CH2NH)4. It is a white solid. It forms Coordination complex, coordination complexes with metal cations and is used to synthesize the chelating agent DOTA (chelator), DOTA which has several medical applications. Being structurally simple, symmetrical, and polyfunctional, cyclen has been widely investigated. Synthesis Some syntheses exploit the Thorpe-Ingold effect to facilitate ring-formation. Illustrative is the reaction of the deprotonated tosylamides with ditosylates: :TsN(CH2CH2NTsNa)2 + TsN(CH2CH2OTs)2 → (TsNCH2CH2)4 The resulting macrocycle can be deprotected with strong acid. Base gives the tetramine. High dilution conditions result in a low reaction rate penalty and this disadvantage is removed in an alternative procedure starting from triethylenetetraamine and dithiooxamide to a amidine, bisamidine – also a bis(2-Imidazoline, imidazoline) – followed by organic reduction, reduc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,3,5-triazinane
Triazinanes are a class of nitrogen-containing heterocycles.''Heterocyclic Chemistry'' T.L. Gilchrist 1985 (1997, The parent molecules' molecular formula is . They exist in three isomeric forms, 1,3,5-triazinanes being common. The triazinanes have six-membered cyclohexane-like ring but with three carbons replaced by nitrogens. Most commonly, the amines are tertiary. See also * 6-membered rings with one nitrogen atom: Piperidine * 6-membered rings with two nitrogen atoms: Diazinane ** Hexahydropyrimidine ** Hexahydropyridazine * Triazine * Borazine Borazine, also known as borazole, inorganic benzene, is an inorganic compound with the chemical formula B3H6N3. In this cyclic compound, the three BH units and three NH units alternate. The compound is isoelectronic and isostructural with benz ... (borazole) References {{Authority control Heterocyclic compounds with 1 ring Nitrogen heterocycles Six-membered rings Polyamines ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,4,7-Triazacyclononane
1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the series include piperazine, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane. Synthesis The ligand is prepared from diethylene triamine as follows by macrocyclization using ethyleneglycol ditosylate. :H2NCH2CH2NHCH2CH2NH2 + 3 TsCl → Ts(H)NCH2CH2N(Ts)CH2CHH2N(H)Ts + 3 HCl :Ts(H)NCH2CH2N(Ts)CH2CH2N(H)Ts + 2 NaOEt → Ts(Na)NCH2CH2N(Ts)CH2CH2N(Na)Ts :Ts(Na)NCHH2CH2N(Ts)CH2CH2N(Na)Ts + TsOCH2CH2OTs + → CH2CH2N(Ts)sub>3 + 2 NaOTs : CH2CH2N(Ts)sub>3 + 3 H2O → H2CH2NHsub>3 + 3 HOTs Coordination chemistry TACN is a popular tridentate ligand. It is threefold symmetric and binds to one face of an octahedron of metalloids and transitio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aziridine
Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry. Structure The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate ''invertomers'', for example the ''cis'' and ''trans'' invertomers of ' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polymer
A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their broad spectrum of properties, both synthetic and natural polymers play essential and ubiquitous roles in everyday life. Polymers range from familiar synthetic plastics such as polystyrene to natural biopolymers such as DNA and proteins that are fundamental to biological structure and function. Polymers, both natural and synthetic, are created via polymerization of many small molecules, known as monomers. Their consequently large molecular mass, relative to small molecule compound (chemistry), compounds, produces unique physical property, physical properties including toughness, high rubber elasticity, elasticity, viscoelasticity, and a tendency to form Amorphous solid, amorphous and crystallization of polymers, semicrystalline structures rath ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyethylenimine
Polyethylenimine (PEI) or polyaziridine is a polymer with repeating units composed of the amine group and two carbon Aliphatic_compound, aliphatic ''CHCH'' spacers. Linear polyethyleneimines contain all Amines#Classification_of_amines, secondary amines, in contrast to branched PEIs which contain primary, secondary and tertiary amino groups. Totally branched, dendrimeric forms were also reported. PEI is produced on an industrial scale and finds many applications usually derived from its polyelectrolyte, polycationic character. Properties The linear PEI is a semi-crystalline solid at room temperature while branched PEI is a fully amorphous polymer existing as a liquid at all molecular weights. Linear polyethyleneimine is soluble in hot water, at low pH, in methanol, ethanol, or chloroform. It is insoluble in cold water, benzene, Diethyl ether, ethyl ether, and acetone. Linear polyethylenimine has a melting point of around 67 °C. Both linear and branched polyethylneimine c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
