Aminoaldehyde
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Aminoaldehyde
Aminoaldehydes and aminoketones are organic compounds that contain an amine functional group as well as either a aldehyde or ketone functional group. These compounds are important in biology and in chemical synthesis. Because of their bifunctional nature, they have attracted much attention from chemists. Tertiary amine derivatives Because primary and secondary amines react with aldehydes and ketones, the most common variety of these aminocarbonyl compounds feature tertiary amines. Such compounds are produced by amination of α-haloketones and α- haloaldehydes. Examples include cathinones, methadone, molindone, pimeclone, ferruginine, and tropinone. Secondary amine derivatives Aminoketones containing secondary amines are typically stable when the ketone is located on a ring, e.g. 4-piperidinone, triacetonamine, acridone Primary amine derivatives Most members of this class are unstable towards self-condensation, however some important examples do exist as intermediates in bi ...
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2-Aminobenzaldehyde
2-Aminobenzaldehyde is an organic compound with the formula C6H4(NH2)CHO. It is one of three isomers of aminobenzaldehyde. It is a low-melting yellow solid that is soluble in water. Preparation and reactions It is usually prepared by reduction of 2-nitrobenzaldehyde with iron or iron(II) sulfate. Like related aminoaldehydes, it is unstable with respect to self-condensation. 2-Aminobenzaldehyde is used to prepare quinolines by the Friedländer synthesis: By template reactions, it also forms trimeric and tetrameric condensation products that have been studied as ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...s. References {{DEFAULTSORT:Aminobenzaldehyde, 2- Benzaldehydes Amines ...
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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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Acridone
Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the ''9'' position. It is a yellow solid. Synthesis and structure The molecule is planar. Optical spectra reveal that the keto tautomer predominates in the gas-phase and in ethanol solution. Acridone can be synthesized by the condensation of aniline and 2-chlorobenzoic acid and subsequently heating of ''N''-phenylanthranilic acid. History One of the first who were able to prove the compound's existence was Karl Drechsler, Student of G. Goldschmiedt, at the k.u.k. Universität Wien (Vienna, Austria) in 1914. Derivatives Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. 3-Chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone has shown promise as an antimalarial drug. See also * Quinacridone Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds e ...
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Amines
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic ...
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Taurine
Taurine (), or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. It is named after Latin (cognate to Ancient Greek ταῦρος, ''taûros'') meaning bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin. It was discovered in human bile in 1846 by Edmund Ronalds. It has many biological roles, such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization, and modulation of calcium signaling. It is essential for cardiovascular function, and development and function of skeletal muscle, the retina, and the central nervous system. It is an unusual example of a naturally occurring sulfonic acid. Chemical and biochemical features Taurine exists as a zwitterion , as verified by X-ray crystallography. The sulfonic aci ...
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Aminoacetone
Aminoacetone is the simplest monopeptide with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable salts, e.g. aminoacetone hydrochloride ( H3C(O)CH2NH3l)). The semicarbazone of the hydrochloride is another bench-stable precursor. Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal. See also * Propanolamines * Aminoaldehydes and aminoketones Aminoaldehydes and aminoketones are organic compounds that contain an amine functional group as well as either a aldehyde or ketone functional group. These compounds are important in biology and in chemical synthesis. Because of their bifunctional ... References Amines Ketones {{amine-stub ...
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Aminoacetaldehyde Diethylacetal
Aminoacetaldehyde diethylacetal is the organic compound with the formula (EtO)2CHCH2NH2. A colorless liquid, it is used as a surrogate for aminoacetaldehyde. See also * Aminoaldehydes and aminoketones Aminoaldehydes and aminoketones are organic compounds that contain an amine functional group as well as either a aldehyde or ketone functional group. These compounds are important in biology and in chemical synthesis. Because of their bifunctional ... References Amines Acetals {{amine-stub ...
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Vancosamine
Vancosamines are aminosugars that are a part of vancomycin and other molecules within the vancomycin family of antibiotics. Vancosamine synthesis is encoded by the vancomycin (''vps'') biosynthetic cluster. Epivancosamine, a closely related aminosugar, is encoded by the chloroeremomycin (''cep'') biosynthetic cluster. History Vancosamine was first isolated by Lomakina ''et al'' in 1968. In 1972, Johnson ''et al'' were the first to identify and completely characterize vancosamine. Epivancosamine was subsequently isolated in 1988 by Hunt ''et al'' at Eli Lilly Biosynthesis The biosynthesis of vancosamine and epivancosamine are identical, except in the last step. The enzymes that catalyze the reactions have been designated EvaA-E. A molecule of TDP-D-glucose enters the pathway via conversion to molecule 1 by an oxidoreductase enzyme and then a dehydratase enzyme. In the next step, EvaA dehydrates molecule 1 by deprotonating at 3-C to form and enolate, which then eliminates 2-O ...
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Amino Sugar
In organic chemistry, an amino sugar (or more technically a 2-amino-2-deoxysugar) is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being ''N''-Acetyl--glucosamine, which is the main component of chitin. Derivatives of amine containing sugars, such as ''N''-acetylglucosamine and sialic acid, whose nitrogens are part of more complex functional groups rather than formally being amines, are also considered amino sugars. Aminoglycosides are a class of antimicrobial compounds that inhibit bacterial protein synthesis. These compounds are conjugates of amino sugars and aminocyclitols. Synthesis From glycals Glycals are cyclic enol ether derivatives of monosaccharides, having a double bond between carbon atoms 1 and 2 of the ring. ''N''-functionalized of glycals at the C2 position, combined with glycosidic bond formation at C1 is a common strategy for the synthesis of amino sugars. T ...
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Glutamate-1-semialdehyde
Glutamate-1-semialdehyde is a molecule formed from by the reduction of tRNA bound glutamate, catalyzed by glutamyl-tRNA reductase. It is isomerized by glutamate-1-semialdehyde 2,1-aminomutase to give aminolevulinic acid in the biosynthesis of porphyrins, including heme and chlorophyll. See also * Glutamate-5-semialdehyde Glutamate-5-semialdehyde is a non-proteinogenic amino acid involved in both the biosynthesis and degradation of proline and arginine (via ornithine), as well as in the biosynthesis of antibiotics, such as carbapenem Carbapenems are a class of ... References Amino acids Aldehydes {{biochem-stub ...
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Self-condensation
Self-condensation is an organic reaction in which a chemical compound containing a carbonyl group acts both as the electrophile and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation as opposed to a mixed aldol condensation in which the electrophile and nucleophile are different species. For example, two molecules of acetone condense to a single compound mesityl oxide in the presence of an ion-exchange resin: :2 CH3COCH3 → (CH3)2C=CH(CO)CH3 + H2O For synthetic uses, this is generally an undesirable, but spontaneous and favored side-reaction of mixed aldol condensation, and special precautions are needed to prevent it. Preventing self-condensation In many cases, self-condensation is an unwanted side-reaction. Therefore, chemists have adopted many ways to prevent this from occurring when performing a crossed aldol reaction. The use of a more reactive electrophile, and a non-enolizable partner If acetophenone and benzaldehyde are put toge ...
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