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TMAO
Trimethylamine ''N''-oxide (TMAO) is an organic compound with the formula (CH3)3NO. It is in the class of amine oxides. Although the anhydrous compound is known, trimethylamine ''N''-oxide is usually encountered as the dihydrate. Both the anhydrous and hydrated materials are white, water-soluble solids. TMAO is found in the tissues of marine crustaceans and marine fish, where it prevents water pressure from distorting proteins and thus killing the animal. The concentration of TMAO increases with the depth at which the animal lives; TMAO is found in high concentrations in the deepest-living described fish species, ''Pseudoliparis swirei'', which was found in the Mariana Trench, at a recorded depth of . TMAO is a product of the oxidation of trimethylamine, a common metabolite of choline in animals. Marine animals Trimethylamine ''N''-oxide is an osmolyte found in molluscs, crustaceans, and all marine fishes and bony fishes. It is a protein stabilizer that serves to counteract ...
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Trimethylaminuria
Trimethylaminuria (TMAU), also known as fish odor syndrome or fish malodor syndrome, is a rare metabolic disorder that causes a defect in the normal production of an enzyme named flavin-containing monooxygenase 3 (''FMO3''). When ''FMO3'' is not working correctly or if not enough enzyme is produced, the body loses the ability to properly convert trimethylamine (TMA) from precursor compounds in food digestion into trimethylamine oxide (TMAO), through a process called ''N''-oxidation. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a fishy odor. Primary trimethylaminuria is caused by genetic mutations that affect the FMO3 function of the liver. Symptoms matching TMAU can also occur when there is no genetic cause, yet excessive TMA excreted - this has been described as secondary trimethylaminuria (TMAU2). TMAU2 can be caused simply by a precursor overload (ingesting too many dietary TMA precursors), hormonal issues related to menstru ...
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Flavin-containing Monooxygenase 3
Flavin-containing monooxygenase 3 (FMO3), also known as dimethylaniline monooxygenase -oxide-forming3 and trimethylamine monooxygenase, is a flavoprotein enzyme () that in humans is encoded by the ''FMO3'' gene. This enzyme catalyzes the following chemical reaction, among others: :trimethylamine + NADPH + H+ + O2 \rightleftharpoons trimethylamine ''N''-oxide + NADP+ + H2O FMO3 is the main flavin-containing monooxygenase isoenzyme that is expressed in the liver of adult humans. The human FMO3 enzyme catalyzes several types of reactions, including: the of primary, secondary, and tertiary amines; the of nucleophilic sulfur-containing compounds; and the of the anti-cancer agent dimethylxanthenone acetic acid ( DMXAA). FMO3 is the primary enzyme in humans which catalyzes the ''N''-oxidation of trimethylamine into trimethylamine ''N''-oxide; FMO1 also does this, but to a much lesser extent than FMO3. Genetic deficiencies of the FMO3 enzyme cause primary trimethylaminuri ...
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Choline
Choline is an essential nutrient for humans and many other animals. Choline occurs as a cation that forms various salts (X− in the depicted formula is an undefined counteranion). Humans are capable of some ''de novo synthesis'' of choline but require additional choline in the diet to maintain health. Dietary requirements can be met by choline per se or in the form of choline phospholipids, such as phosphatidylcholine. Choline is not formally classified as a vitamin despite being an essential nutrient with an amino acid–like structure and metabolism. In most animals, choline phospholipids are necessary components in cell membranes, in the membranes of cell organelles, and in very low-density lipoproteins. Choline is required to produce acetylcholine – a neurotransmitter – and ''S''-adenosylmethionine (SAM), a universal methyl donor. Upon methylation SAM is transformed into homocysteine. Symptomatic choline deficiency causes non-alcoholic fatty liver disease and muscl ...
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Greenland Shark
The Greenland shark (''Somniosus microcephalus''), also known as the gurry shark, grey shark, or by the Kalaallisut name ''eqalussuaq'', is a large shark of the family Somniosidae ("sleeper sharks"), closely related to the Pacific and southern sleeper sharks. The distribution of this species is mostly restricted to the waters of the North Atlantic Ocean and Arctic Ocean; however, more recent evidence indicates that at great depths it may range as far south as the Caribbean. The Greenland shark has the longest known lifespan of all vertebrate species (estimated to be between 250 and 500 years), and is among the largest extant species of shark. It is a generalist feeder, consuming a variety of available foods. As an adaptation to living at depth, it has a high concentration of trimethylamine ''N''-oxide in its tissues, which causes the meat to be toxic. Greenland shark flesh, treated to reduce toxin levels, is eaten in Iceland as a delicacy known as '' kæstur hákarl''. As ...
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Trimethylamine
Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a colorless, hygroscopic, and flammable tertiary amine. It is a gas at room temperature but is usually sold as a 40% solution in water. (It is also sold in pressurized gas cylinders.) TMA is a nitrogenous base and can be readily protonated to give the trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications. TMA is widely used in industry: it is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators or herbicides, strongly basic anion exchange resins, dye leveling agents, and a number of basic dyes. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact. At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish. In humans, ing ...
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Osmolyte
Osmolytes are low-molecular weight organic compounds that influence the properties of biological fluids. Their primary role is to maintain the integrity of cells by affecting the viscosity, melting point, and ionic strength of the aqueous solution. When a cell swells due to external osmotic pressure, membrane channels open and allow efflux of osmolytes which carry water with them, restoring normal cell volume. Osmolytes also interact with the constituents of the cell, e.g. they influence protein folding. Common osmolytes include amino acids, sugars and polyols, methylamines, methylsulfonium compounds, and urea. Case studies Natural osmolytes that can act as osmoprotectants include trimethylamine ''N''-oxide (TMAO), dimethylsulfoniopropionate, sarcosine, betaine, glycerophosphorylcholine, myo-inositol, taurine, glycine, and others. Remarkably, TMAO has the capacity to restore glucocorticoid binding to mutant receptors. Bacteria accumulate osmolytes for protection against a ...
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Debye
The debye (symbol: D) (; ) is a CGS unit (a non- SI metric unit) of electric dipole momentTwo equal and opposite charges separated by some distance constitute an electric dipole. This dipole possesses an electric dipole moment whose value is given as charge times length of separation, it is a vector whose direction is in the direction of the unit vector of the position vector of the positive charge w.r.t negative charge: :p = ''q''r. named in honour of the physicist Peter J. W. Debye. It is defined as statcoulomb-centimeters.The statcoulomb is also known as the franklin or electrostatic unit of charge. :1 statC = 1 Fr = 1 esu = 1 cm3/2⋅g1/2⋅s−1. Historically the debye was defined as the dipole moment resulting from two charges of opposite sign but an equal magnitude of 10−10 statcoulomb10−10 statcoulomb corresponds to approximately 0.2083 units of elementary charge. (generally called e.s.u. (electrostatic unit) in older scienti ...
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Stoichiometry
Stoichiometry refers to the relationship between the quantities of reactants and products before, during, and following chemical reactions. Stoichiometry is founded on the law of conservation of mass where the total mass of the reactants equals the total mass of the products, leading to the insight that the relations among quantities of reactants and products typically form a ratio of positive integers. This means that if the amounts of the separate reactants are known, then the amount of the product can be calculated. Conversely, if one reactant has a known quantity and the quantity of the products can be empirically determined, then the amount of the other reactants can also be calculated. This is illustrated in the image here, where the balanced equation is: : Here, one molecule of methane reacts with two molecules of oxygen gas to yield one molecule of carbon dioxide and two molecules of water. This particular chemical equation is an example of complete combustion. ...
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Oxidizing Agents
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxidizer is any substance that oxidizes another substance. The oxidation state, which describes the degree of loss of electrons, of the oxidizer decreases while that of the reductant increases; this is expressed by saying that oxidizers "undergo reduction" and "are reduced" while reducers "undergo oxidation" and "are oxidized". Common oxidizing agents are oxygen, hydrogen peroxide and the halogens. In one sense, an oxidizing agent is a chemical species that undergoes a chemical reaction in which it gains one or more electrons. In that sense, it is one component in an oxidation–reduction (redox) reaction. In the second sense, an oxidizing agent is a chemical species that transfers electronegative atoms, usually oxygen, to a substrate. Comb ...
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Nutrition
Nutrition is the biochemical and physiological process by which an organism uses food to support its life. It provides organisms with nutrients, which can be metabolized to create energy and chemical structures. Failure to obtain sufficient nutrients causes malnutrition. Nutritional science is the study of nutrition, though it typically emphasizes human nutrition. The type of organism determines what nutrients it needs and how it obtains them. Organisms obtain nutrients by consuming organic matter, consuming inorganic matter, absorbing light, or some combination of these. Some can produce nutrients internally by consuming basic elements, while some must consume other organisms to obtain preexisting nutrients. All forms of life require carbon, energy, and water as well as various other molecules. Animals require complex nutrients such as carbohydrates, lipids, and proteins, obtaining them by consuming other organisms. Humans have developed agriculture and cooking to repla ...
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Lipid Disorders
Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology. Lipids may be broadly defined as hydrophobic or amphiphilic small molecules; the amphiphilic nature of some lipids allows them to form structures such as vesicles, multilamellar/unilamellar liposomes, or membranes in an aqueous environment. Biological lipids originate entirely or in part from two distinct types of biochemical subunits or "building-blocks": ketoacyl and isoprene groups. Using this approach, lipids may be divided into eight categories: fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, saccharolipids, and polyketides (derived from condensa ...
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Amine Oxides
In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that contains the functional group , a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-group side chains attached to N. Sometimes it is written as →O or, incorrectly, as . In the strict sense, the term ''amine oxide'' applies only to oxides of tertiary amines. Sometimes it is also used for the analogous derivatives of primary and secondary amines. Examples of amine oxides include pyridine-''N''-oxide, a water-soluble crystalline solid with melting point 62–67 °C, and ''N''-methylmorpholine ''N''-oxide, which is an oxidant. Applications Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners. Alkyl dimethyl amine oxide (chain lengths C10–C16) is the most commercially used amine oxide. They are considered a high production volume class of ...
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