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Eritadenine
Eritadenine is a chemical compound found in shiitake mushrooms. Eritadenine is an inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH) and has hypocholesterolemic activity. Synthesis The structure is a purine alkylated with an oxidized sugar fragment. Ring opening of the protected lactone (1), derived from erythrose with sodium phthalimide gives the acid 2; hydrazinolysis (cf Gabriel synthesis) then leads to the amino acid 3. Displacement of chlorine in pyrimidine 4 by the amine function on 3 serves to attach the future imidazole nitrogen and the sugar-derived sidechain (5). The nitro group is then reduced by catalytic hydrogenation, the resulting primary amine is the most basic and is selectively formylated with formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est .... ...
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Shiitake
The shiitake (alternate form shitake) (; ''Lentinula edodes'') is an edible mushroom native to East Asia, which is now cultivated and consumed around the globe. It is considered a medicinal mushroom in some forms of traditional medicine. Taxonomy and naming The fungus was first described scientifically as ''Agaricus edodes'' by Miles Joseph Berkeley in 1877. It was placed in the genus '' Lentinula'' by David Pegler in 1976. The fungus has acquired an extensive synonymy in its taxonomic history: *''Agaricus edodes'' Berk. (1878) *''Armillaria edodes'' (Berk.) Sacc. (1887) *''Mastoleucomychelloes edodes'' (Berk.) Kuntze (1891) *''Cortinellus edodes'' (Berk.) S.Ito & S.Imai (1938) *''Lentinus edodes'' (Berk.) Singer (1941) *''Collybia shiitake'' J.Schröt. (1886) *''Lepiota shiitake'' (J.Schröt.) Nobuj. Tanaka (1889) *''Cortinellus shiitake'' (J.Schröt.) Henn. (1899) *''Tricholoma shiitake'' (J.Schröt.) Lloyd (1918) *''Lentinus shiitake'' (J.Schröt.) Singer (1936) *''Le ...
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S-adenosyl-L-homocysteine Hydrolase
S-adenosyl-L-homocysteine hydrolase () (AdoHcyase) is an enzyme of the activated methyl cycle, responsible for the reversible hydration of S-adenosyl-L-homocysteine into adenosine and homocysteine. AdoHcyase is a ubiquitous enzyme which binds and requires NAD+ as a cofactor. AdoHcyase is a highly conserved protein of about 430 to 470 amino acids. The family contains a glycine-rich region in the central part of AdoHcyase; a region thought to be involved in NAD-binding. AdoHcyase is significantly associated with adenosine deaminase deficiency, which classically manifests in severe combine immunodeficiency (SCID). Accumulated adenosine derivatives, dATPs, irreversibly bind to and inhibit AdoHcyase, promoting the buildup of S-adenosyl-L-homocystine (due to equilibrium constant favors S-adenosyl-L-homocystine), a potent inhibitor of methyl transfer reactions. This protein may use the morpheein model of allosteric regulation In biochemistry, allosteric regulation (or alloster ...
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Erythrose
Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D -threose. Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869), and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red"). Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway and the Calvin cycle. Oxidative bacteria can be made to use erythrose as its sole energy source. See also * Erythritol Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula ... References {{Carbohydrates Aldotetroses ...
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Sodium Phthalimide
Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable isotope is 23Na. The free metal does not occur in nature, and must be prepared from compounds. Sodium is the sixth most abundant element in the Earth's crust and exists in numerous minerals such as feldspars, sodalite, and halite (NaCl). Many salts of sodium are highly water-soluble: sodium ions have been leached by the action of water from the Earth's minerals over eons, and thus sodium and chlorine are the most common dissolved elements by weight in the oceans. Sodium was first isolated by Humphry Davy in 1807 by the electrolysis of sodium hydroxide. Among many other useful sodium compounds, sodium hydroxide (lye) is used in soap manufacture, and sodium chloride (edible salt) is a de-icing agent and a nutrient for animals including hum ...
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Gabriel Synthesis
The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel. The Gabriel reaction has been generalized to include the alkylation of sulfonamides and imides, followed by deprotection, to obtain amines (see Alternative Gabriel reagents). The alkylation of ammonia is often an unselective and inefficient route to amines. In the Gabriel method, phthalimide anion is employed as a surrogate of H2N−. Traditional Gabriel synthesis In this method, the sodium or potassium salt of phthalimide is ''N''-alkylated with a primary alkyl halide to give the corresponding ''N''-alkylphthalimide. Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. Alternatively the workup may be via the Ing–Manske procedure, involving reaction with hydrazine. This method produces a precipitate of phthalhydrazide ( ...
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Pyrimidine
Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The other diazines are pyrazine (nitrogen atoms at the 1 and 4 positions) and pyridazine (nitrogen atoms at the 1 and 2 positions). In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U). Occurrence and history The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. It is also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. Although pyrimidine derivatives such as alloxan were known in the early 19th century, a laboratory synthesis of a pyrimidine was not carried out until 1879, when Grimaux reported ...
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Formic Acid
Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol. Natural occurrence In nature, formic acid is found in most ants and in stingless bees of the genus '' Oxytrigona''. Wood ants from the genus '' Formica'' can spray formic acid on their prey or to defend the nest. The puss moth caterpillar (''Cerura vinula'') will spray it as well when threatened by predators. It is also found in the trichomes of stinging nettle (''Urtica dioica''). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21mg per 100g), apple (2mg per 100g) and kiwi (1mg per 100g), as well as in many vegetables, namely onion (45mg per 100g), eggplant (1.34 mg per 100g) an ...
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Alkaloids
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , ,