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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.
(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 .
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.
[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 ...
Dactylifric acid (also known as dattelic acid or 5-O-caffeoylshikimic acid [2] [3] [4]) is an ester derived from caffeic acid and shikimic acid. It and its isomers are enzymic browning substrates found in dates (Phoenix dactylifera fruits). [3] [5] Some older sources identify dactylifric acid as 3-O-caffeoylshikimic acid. [5]
Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir. [3] Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals.
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.