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In the pharmaceutical industry, shikimic acid from the Chinese star anise (Illicium verum) is used as a base material for production of oseltamivir . Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and in general found in very low concentrations.
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 ...
Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals. As with shikimic acid, aminoshikimic acid is an attractive candidate for use as the core scaffold for synthesis of combinatorial libraries.
[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 ...
(6S)-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway. [1] It may be used against Plasmodium falciparum, the causative agent of malaria. [2] The molecule is targeting the enzymes of the shikimate pathway. This metabolic pathway is not present in mammals.
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]
4-Hydroxyphenylglycine (HPG) is a non-proteogenic amino acid found in vancomycin and related glycopeptides. HPG is synthesized from the shikimic acid pathway and requires four enzymes to synthesize: [1] Both L- and D-HPG are used in the vancomycin class of antibiotics.
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