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Encyclopedia > Shikimic acid
As of 16:11, 5 May 2006 (UTC), the article page was linked from Slashdot, a high-traffic Internet site.
All prior and subsequent edits are noted in the revision history.
Shikimic acid
Chemical structure of shikimic acid
Chemical name (3R,4S,5R)-3,4,5-Trihydroxy-
1-cyclohexenecarboxylic acid
Chemical formula C7H10O5
Molecular mass 174.15 g/mol
Melting point 185–187 °C
CAS number [138-59-0]
EINECS number 205-334-2
Disclaimer and references

Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, Illicium anisatum), from which it was first isolated. Image File history File links Web_traffic. ... Image File history File links Download high resolution version (1591x1652, 25 KB) Summary Description: Skeletal formula of shikimic acid ((3R,4S,5R)-3,4,5-Trihydroxy- 1-cyclohexenecarboxylic acid; C7H10O5). ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... // An ion is an atom, group of atoms, or subatomic particle with a net electric charge. ... Japanese star anise (Illicium anisatum, also Illicium japonicum and Illicium religiosum), is a tree similar to Chinese star anise. ...


Shikimic acid is a precursor for:

In pharmaceutical industry, shikimic acid from chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations. The low isolation yield of shikimic acid from chinese star anise is blamed for the 2005 shortage of oseltamivir. Shikimic acid can also be extracted from the seeds of the sweetgum fruit, which is abundant in North America, in yields of around 1.5%, so just 4 kg of sweetgum seeds are enough for 14 packages of Tamiflu. By comparison Star anise has been reported to yield 3 to 7% shikimic acid. Recently biosynthetic pathways in E Coli have been enhanced to allow the organism to accumulate enough material to be used commercially. In chemistry, an amino acid is any molecule that contains both amino and carboxylic acid functional groups. ... The alpha-amino acid Phenylalanine exists in two forms, the D- and L- forms, which are enantiomers (mirror-image molecules) of each other. ... Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in cheese), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins. ... Indole is an aromatic heterocyclic organic compound. ... Tryptophan is an amino acid and essential in human nutrition. ... An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and animals. ... A metabolite is the product of metabolism. ... Tannins are astringent, bitter-tasting plant polyphenols that bind and precipitate proteins. ... Lignin is a chemical compound that is an integral part of the cell walls of some cells, e. ... Binomial name Illicium verum Hook. ... Oseltamivir (INN) (IPA: ) is an antiviral drug used in the treatment and prophylaxis of both Influenzavirus A and Influenzavirus B. Like zanamivir, oseltamivir is a neuraminidase inhibitor. ... An autotroph (in Greek eauton = self and trophe = nutrition) is an organism that produces its own cell mass and organic compounds from carbon dioxide as sole carbon source, using either light or chemical compounds as a source of energy. ...


Biosynthesis

Phosphoenol pyruvate and erythrose-4-phosphate react to form 3-desoxy-2-keto-arabinoheptonate-7-phosphate. This is then oxidised by NAD+ to form 3-dehydroquinate. Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ... 3-Dehydroquinic acid is the first cyclic intermediate of the shikimate pathway. ...


Image File history File links Download high resolution version (1544x578, 18 KB) Description: First half of the biosynthesis of shikimate. ...


3-Dehydroquinate is dehydrated to 3-dehydroshikimate, which is reduced by NADPH to shikimate. 3-Dehydroquinic acid is the first cyclic intermediate of the shikimate pathway. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ...


Image File history File links Download high resolution version (1498x330, 12 KB) Description: Second half of the biosynthesis of shikimate. ...


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  Results from FactBites:
 
Nat' Academies Press, Carbon Management: Implications for R & D in the Chemical Sciences and Technology (A Workshop ... (963 words)
Shikimic acid, in contrast to p-hydroxybenzoic acid, is not toxic to microbes.
Dehydration of shikimic acid required the use of acetic acid as the reaction solvent to avoid the high concentrations of mineral acid (8-12 M) that would be required to catalyze dehydration of shikimic acid in aqueous solution.
Attempts to convert shikimic acid in clarified fermentor broth failed to produce significant yields of p-hydroxybenzoic acid, thus necessitating that shikimic acid be isolated from the fermentor broth prior to its acidcatalyzed dehydration.
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