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Biosynthesis Of Cocaine
The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core. Biosynthesis of ''N''-methyl-pyrrolinium cation The biosynthesis begins with L-glutamine, which is derived from L-ornithine in plants. The roles of L-ornithine and L-arginine was confirmed by Edward Leete. Ornithine then undergoes a PLP-dependent decarboxylation to form putrescine. In animals, however, the urea cycle derives putrescine from ornithine. L-Ornithine is converted to L-arginine, which is then decarboxylated via PLP to form agmatine. Hydrolysis of the imine derives ''N''-carbamoy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Kokain - Cocaine
Cocaine is a naturally occurring organic compound, an alkaloid, present in the leaves of the coca plant. * Cocaine (data page) Cocaine may also refer to: Arts and entertainment * ''Cocaine'' (film), a 1922 British crime film directed by Graham Cutts * ''The Pace That Kills'' (1935 film), also known as Cocaine Madness and The Cocaine Fiends, a 1935 film directed by William A. O'Conner * '' Cocaine: An Unauthorized Biography'', a 2002 book by Dominic Streatfeild * ''Cocaine Blues'' (novel), by Kerry Greenwood (1989) Music * ''Cocaine'' (album), a 2009 album by Z-Ro * " Cocaine" (song), a 1976 song by J.J. Cale, later recorded by Eric Clapton and Nazareth * "Cocaine", a poem by Patti Smith in her 1972 book '' Seventh Heaven'' * "Coke'n", a 2002 song by Izzy Stradlin on his album ''On Down the Road'' * "Cocaine Blues", Other uses * Cocaine (PaaS), an open source project * Cocaine (drink), a highly caffeinated energy drink that does not contain the alkaloid cocaine * Honey Cocai ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diamine Oxidase
Diamine oxidase (DAO), also known "amine oxidase, copper-containing, 1" (AOC1), formerly called histaminase, is an enzyme () involved in the metabolism, oxidation, and inactivation of histamine and other polyamines such as putrescine or spermidine in animals. It belongs to the amine oxidase (copper-containing) (AOC) family of amine oxidase enzymes. In humans, DAO it is encoded by ''AOC1'' gene. The highest levels of DAO expression are observed in the digestive tract and the placenta. In humans, a certain subtype of cells of the placenta, namely the extravillous trophoblasts, express the enzyme and secrete it into the blood stream of a pregnant woman. Lowered diamine oxidase values in maternal blood in early pregnancy might be an indication for trophoblast-related pregnancy disorders like early-onset preeclampsia. Normally the enzyme is not or only very scarcely present in the blood circulation of humans, but it increases vastly in pregnant women suggesting a protective me ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cinnamic Acid
Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a ''cis'' and a ''trans'' isomer, although the latter is more common. Occurrence and production Biosynthesis Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. Natural occurrence It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter. Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester ( ethyl cinnamate) are flavor componen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenylalanine
Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the skin pigment melanin. It is encoded by the codons UUU and UUC. Phenylalanine is found naturally in the milk of mammals. It is used in the manufacture of food and drink products and sold as a nutritional supplement for its analgesic and antidepressant effects. It is a direct precursor to the neuromodulator phenethylamine, a commonly used dietary supplement. As an essential amino acid, phenylalanine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzoyl
In organic chemistry, benzoyl (, ) is the functional group with the formula C6H5CO-. It can be viewed as benzaldehyde missing one hydrogen. The term "benzoyl" should not be confused with benzyl, which has the formula C6H5CH2. The benzoyl group is given the symbol "Bz". Benzyl is commonly abbreviated "Bn". Sources Benzoyl chloride is a favored source of benzoyl groups, being used to prepare benzoyl ketones, benzamides (benzoyl amides), and benzoate esters. The source of many naturally occurring benzoyl compounds is the thioester benzoyl-CoA. Irradiation of benzil generates benzoyl radicals, which have the formula PhCO. Benzoyl compounds Many ketones contain the benzoyl group. They have the formula C6H5CO–R, an important example being benzophenone. Benzoyl esters and amides are common in organic chemistry. The esters are used as a protecting groups in organic synthesis, which can be easily removed by hydrolysis in dilute basic BASIC (Beginners' All-purpose Symbolic I ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
NADPH
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NADPH as a reducing agent ('hydrogen source'). It is used by all forms of cellular life. NADPH is the reduced form of NADP. NADP differs from NAD by the presence of an additional phosphate group on the 2' position of the ribose ring that carries the adenine moiety. This extra phosphate is added by NAD+ kinase and removed by NADP+ phosphatase. Biosynthesis NADP In general, NADP+ is synthesized before NADPH is. Such a reaction usually starts with NAD+ from either the de-novo or the salvage pathway, with NAD+ kinase adding the extra phosphate group. ADP-ribosyl cyclase allows for synthesis from nicotinamide in the salvage pathway, and NADP+ phosphatase can convert NADPH back to NADH to maintain a balance. Some forms of the NAD+ kinase, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and water molecule to split into two parts. I ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Racemic
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. History The first known racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid. He manually separated the crystals of a mixture by hand, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt that gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from the macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an ''enantiomerically pure'' or ''enantiopure'' compound. Etymology From racemic acid found in grapes; from Latin ''racemus'', m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropinone
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone. Synthesis The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps to introduce the nitrogen bridge; the overall yield for the synthesis path is only 0.75%. Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine. Robinson's "double Mannich" reaction The 1917 synthesis by Robinson is considered a classic in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nucleophile
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. ''Nucleophilic'' describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. History The terms ''nucleophile'' and ''electrophile'' were introduced by Christopher Kelk Ingold in 1933, replacing the terms ''anionoid'' and ''cation ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mannich Reaction
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl () functional group by formaldehyde () and a primary or secondary amine () or ammonia (). The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich. center, 500px, Scheme 1 - Ammonia or an amine reacts with formaldehyde and an alpha acidic proton of a carbonyl compound to a beta amino carbonyl compound. The Mannich reaction starts with the nucleophilic addition of an amine to a carbonyl group followed by dehydration to the Schiff base. The Schiff base is an electrophile which reacts in a second step in an electrophilic addition with an enol formed from a carbonyl compound containing an acidic alpha-proton. The Man ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cuscohygrine
Cuscohygrine is a pyrrolidine alkaloid found in coca. It can also be extracted from plants of the family Solanaceae, including ''Atropa belladonna'' (deadly nightshade), '' Datura innoxia'' and ''Datura stramonium'' (jimson weed). Cuscohygrine usually occurs along with other, more potent alkaloids such as atropine or cocaine. Cuscohygrine, along with the related metabolite hygrine, was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca leaves (also known as Cusco-leaves). Cuscohygrine is an oil that can be distilled without decomposition only in vacuum. It is soluble in water. It also forms a crystalline tri hydrate which melts at 40–41 °C. See also * Coca alkaloid Coca alkaloids are the alkaloids found in the coca plant, ''Erythroxylum coca''.Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop. Emanuel L. Johnson and Stephen D. Emche, Ann. Bot., 1994, volume 73, issue 6, page ...s * Dihydrocuscohygri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
