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Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms.
The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine). This pathway is not found in mammals.
The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. [1] Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid , which is the central intermediate in ...
[23] [24] The aromatic amino acid phenylalanine, synthesized in the shikimic acid pathway, is the common precursor of phenol containing amino acids and phenolic compounds. In plants, the phenolic units are esterified or methylated and are submitted to conjugation , which means that the natural phenols are mostly found in the glycoside form ...
Shikimic acid, biosynthetic precursor to aromatic amino acids, is a close relative of quinic acid. This substance was isolated for the first time in 1790 by German pharmacist Friedrich Christian Hofmann in Leer from Cinchona. [3] Its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863. [4]
Polyphenols incorporate smaller parts and building blocks from simpler natural phenols, which originate from the phenylpropanoid pathway for the phenolic acids or the shikimic acid pathway for gallotannins and analogs. Flavonoids and caffeic acid derivatives are biosynthesized from phenylalanine and malonyl-CoA.
Biosynthesis of shikimic acid from 3-dehydroquinate Gallic acid is also formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate . This latter compound spontaneously rearranges to gallic acid.
Star anise oil is a highly fragrant oil used in cooking, perfumery, soaps, toothpastes, mouthwashes, and skin creams. Until 2012, when they switched to using genetically modified E. coli, Roche Pharmaceuticals used up to 90% of the world's annual star anise crop to produce oseltamivir (Tamiflu) via shikimic acid. [3]
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