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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.
These fronds are edible, but can be roasted to remove shikimic acid. [11] Shikimic acid is also the glycoside part of some hydrolysable tannins. The acid is highly soluble in water and insoluble in nonpolar solvents, and this is why shikimic acid is active only against Gram-positive bacteria, due to outer cell membrane impermeability of Gram ...
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 ...
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.
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]
In contrast, animals and humans lack this pathway hence products of this biosynthetic route are essential amino acids that must be obtained through an animal's diet. There are seven enzymes that play a role in this pathway. Shikimate dehydrogenase (also known as 3-dehydroshikimate dehydrogenase) is the fourth step of the seven step process.