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Erysodienone
Erysodienone is a key precursor in the biosynthesis of many ''Erythrina''-produced alkaloids. Early work was done by Derek Barton and co-workers to illustrate the biosynthetic pathways towards erythrina alkaloids. It was demonstrated that erysodienone could be synthesized from simple starting materials by a similar approach as its biosynthetic pathway, which led to the development of the biomimetic synthesis of erysodienone. Synthesis The biosynthesis of erysodienone involves a key step of Oxidative coupling, oxidative phenol coupling. Starting with S-norprotosinomenine precursor A, Pericyclic reaction, cyclization via oxidative phenol coupling forms intermediate B, which in turn can be rearranged to form intermediate C. Hydrogenation of C forms the diphenoquinone intermediate E. An Intramolecular reaction, intramolecular Michael addition reaction converts E to the final product, erysodienone. : A biomimetic synthesis route for erysodienone was developed based on a similar oxidat ...
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Erythrina
''Erythrina'' is a genus of plants in the pea family, Fabaceae. It contains about 130 species, which are distributed in tropical and subtropical regions worldwide. They are trees, with the larger species growing up to in height. These species are known for their large flowers with long and bright red or orange petals. Taxonomy The generic name is derived from the Greek word , meaning "red", referring to the flower color of certain species. Common names Particularly in horticulture, the name coral tree is used as a collective term for these plants. Flame tree is another vernacular name, but may refer to a number of unrelated plants as well. Many species of ''Erythrina'' have bright red flowers, and this may be the origin of the common name. However, the growth of the branches can resemble the shape of sea coral rather than the color of '' Corallium rubrum'' specifically, and this is an alternative source for the name. Other popular names, usually local and particular to ...
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Biosynthesis
Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthesis) serve as enzyme substrate (chemistry), substrates, with conversion by the living organism either into simpler or more complex Product (chemistry), products. Examples of biosynthetic pathways include those for the production of amino acids, lipid membrane components, and nucleotides, but also for the production of all classes of biological macromolecules, and of acetyl-coenzyme A, adenosine triphosphate, nicotinamide adenine dinucleotide and other key intermediate and transactional molecules needed for metabolism. Thus, in biosynthesis, any of an array of Chemical compound, compounds, from simple to complex, are converted into other compounds, and so it includes both the catabolism and anabolism (building up and breaking down) of comple ...
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Biomimetic Synthesis Of Erysodienone
Biomimetics or biomimicry is the emulation of the models, systems, and elements of nature for the purpose of solving complex human problems. The terms "biomimetics" and "biomimicry" are derived from (''bios''), life, and μίμησις ('' mīmēsis''), imitation, from μιμεῖσθαι (''mīmeisthai''), to imitate, from μῖμος (''mimos''), actor. A closely related field is bionics. Nature has gone through evolution over the 3.8 billion years since life is estimated to have appeared on the Earth. It has evolved species with high performance using commonly found materials. Surfaces of solids interact with other surfaces and the environment and derive the properties of materials. Biological materials are highly organized from the molecular to the nano-, micro-, and macroscales, often in a hierarchical manner with intricate nanoarchitecture that ultimately makes up a myriad of different functional elements. Properties of materials and surfaces result from a complex interpla ...
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Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of py ...
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K3Fe(CN)6
Potassium ferricyanide is the chemical compound with the formula K3 e(CN)6 This bright red salt contains the octahedrally coordinated 3−">e(CN)6sup>3− ion. It is soluble in water and its solution shows some green-yellow fluorescence. It was discovered in 1822 by Leopold Gmelin. Preparation Potassium ferricyanide is manufactured by passing chlorine through a solution of potassium ferrocyanide. Potassium ferricyanide separates from the solution: :2 K4 e(CN)6+ Cl2 → 2 K3 e(CN)6+ 2 KCl Structure Like other metal cyanides, solid potassium ferricyanide has a complicated polymeric structure. The polymer consists of octahedral e(CN)6sup>3− centers crosslinked with K+ ions that are bound to the CN ligands. The K+---NCFe linkages break when the solid is dissolved in water. Applications The compound is also used to harden iron and steel, in electroplating, dyeing wool, as a laboratory reagent, and as a mild oxidizing agent in organic chemistry. Photography Blueprint, cya ...
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Structure Of Erysodienone And Its Proposed Biosynthetic Pathway
A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as biological organisms, minerals and chemicals. Abstract structures include data structures in computer science and musical form. Types of structure include a hierarchy (a cascade of one-to-many relationships), a network featuring many-to-many links, or a lattice featuring connections between components that are neighbors in space. Load-bearing Buildings, aircraft, skeletons, anthills, beaver dams, bridges and salt domes are all examples of load-bearing structures. The results of construction are divided into buildings and non-building structures, and make up the infrastructure of a human society. Built structures are broadly divided by their varying design approaches and standards, into categories including building structures, arc ...
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Michael Addition
In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon–carbon bonds. The Michael addition is an important atom-economical method for diastereoselective and enantioselective C–C bond formation, and many asymmetric variants exist : In this general Michael addition scheme, either or both of R and R' on the nucleophile (the Michael donor) represent electron-withdrawing substituents such as acyl, cyano, nitro, or sulfone groups, which make the adjacent methylene hydrogen acidic enough to form a carbanion when reacted with the base, ''B:''. For the alkene (the Michael acceptor), the R" substituent is usually a carbonyl, which makes the co ...
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Intramolecular Reaction
In chemistry, intramolecular describes a Chemical process, process or characteristic limited within the Chemical structure, structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Relative rates In intramolecular organic reactions, two reaction sites are contained within a single molecule. This configuration elevates the effective concentration of the reacting partners resulting in high reaction rates. Many intramolecular reactions are observed where the intermolecular version does not take place. Intramolecular reactions, especially ones leading to the formation of 5- and 6-membered rings, are rapid compared to an analogous intermolecular process. This is largely a consequence of the reduced entropic cost for reaching the transition state of ring formation and the absence of significant strain associated with formation of rings of these sizes. For the formation of different ring sizes via cyclization of substrates of varying tether ...
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Pericyclic Reaction
In organic chemistry, a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and the bond orbitals involved in the reaction overlap in a continuous cycle at the transition state. Pericyclic reactions stand in contrast to ''linear reactions'', encompassing most organic transformations and proceeding through an acyclic transition state, on the one hand and '' coarctate reactions'', which proceed through a doubly cyclic, concerted transition state on the other hand. Pericyclic reactions are usually rearrangement or addition reactions. The major classes of pericyclic reactions are given in the table below (the three most important classes are shown in bold). Ene reactions and cheletropic reactions are often classed as group transfer reactions and cycloadditions/cycloeliminations, respectively, while dyotropic reactions and group transfer reactions (if ene reactions ar ...
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Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated and unsaturated compounds, saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces Double bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same cataly ...
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Phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. It is acutely toxic and is considered a health hazard. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds, and is a liquid when manufactured. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceuti ...
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