Shikimic acid

shikimateshikimate pathwayshikimicshikimic acid pathway
Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid.wikipedia
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3-Dehydroshikimic acid

3-dehydroshikimate3-DHS
DHQ is dehydrated to 3-dehydroshikimic acid by the enzyme 3-dehydroquinate dehydratase, which is reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor.
3-Dehydroshikimic acid is a chemical compound related to shikimic acid.

Cyclitol

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid.
Some cyclitol (e.g. quinic or shikimic acid) are parts of hydrolysable tannins.

Hydrolysable tannin

hydrolyzable tanninhydrolyzable tanninshydrolysable type
Shikimic acid is also the glycoside part of some hydrolysable tannins.
At the center of a hydrolyzable tannin molecule, there is a carbohydrate (usually D-glucose but also cyclitols like quinic or shikimic acids).

Shikimate dehydrogenase

DHQ is dehydrated to 3-dehydroshikimic acid by the enzyme 3-dehydroquinate dehydratase, which is reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor. The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.
Thus, the two substrates of this enzyme are shikimate and NADP +, whereas its 3 products are 3-dehydroshikimate, NADPH, and H + . This enzyme participates in phenylalanine, tyrosine and tryptophan biosynthesis.

Shikimate kinase

The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.
Shikimate kinase is an enzyme that catalyzes the ATP-dependent phosphorylation of shikimate to form shikimate 3-phosphate.

Johann Frederik Eijkman

Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman.
During his stay in Japan, he was the first to isolate shikimic acid in 1885 from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum).

3-dehydroquinate dehydratase

DHQ is dehydrated to 3-dehydroshikimic acid by the enzyme 3-dehydroquinate dehydratase, which is reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor. The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.
The shikimate pathway was determined to be a major biosynthetic route for the production of aromatic amino acids through the research of Bernhard Davis and David Sprinson.

Illicium anisatum

Japanese star aniseShikimi
Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman.
Shikimic acid, a substance also present in Japanese star anise, is so-called after the plant's Japanese name.

Illicium verum

star aniseStar Anisstar aniseed
In the pharmaceutical industry, shikimic acid from the Chinese star anise (Illicium verum) is used as a base material for production of oseltamivir (Tamiflu).
About 90% of the world's star anise crop is used for extraction of shikimic acid, a chemical intermediate used in the synthesis of oseltamivir (Tamiflu).

Chorismate mutase

c'''horismate mutaseCM_mono2
Prephenic acid is then synthesized by a Claisen rearrangement of chorismate by Chorismate mutase.
In enzymology, chorismate mutase is an enzyme that catalyzes the chemical reaction for the conversion of chorismate to prephenate in the pathway to the production of phenylalanine and tyrosine, also known as the shikimate pathway.

Protecting group

protective groupdeprotectionprotected
Protecting groups are more commonly used in small-scale laboratory work and initial development than in industrial production processes because their use adds additional steps and material costs to the process.
However, the availability of a cheap chiral building block can overcome these additional costs (e.g. shikimic acid for oseltamivir).

Prephenic acid

prephenatedisodium prephenate
Prephenic acid is then synthesized by a Claisen rearrangement of chorismate by Chorismate mutase.
Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.

Chorismate synthase

The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.
Chorismate synthase catalyzes the last of the seven steps in the shikimate pathway which is used in prokaryotes, fungi and plants for the biosynthesis of aromatic amino acids.

Phosphoenolpyruvic acid

phosphoenolpyruvatePEPphosphoenol pyruvate
Phosphoenolpyruvate and erythrose-4-phosphate react to form 3-deoxy- D -arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase. The pathway starts with two substrates, phosphoenol pyruvate and erythrose-4-phosphate and ends with chorismate, a substrate for the three aromatic amino acids.
PEP may be used for the synthesis of chorismate through the shikimate pathway.

Aminoshikimate pathway

* Aminoshikimate pathway, a novel variation of the shikimate pathway
The pathway is a novel variation of the shikimate pathway.

List of IARC Group 3 carcinogens

Group 3IARC Group 3 carcinogenclass 3 carcinogen
It appears in the list of Group 3 carcinogens of the International Agency for Research on Cancer.
Shikimic acid

EPSP synthase

5-enolpyruvylshikimate-3-phosphate synthase3-phosphoshikimate 1-carboxyvinyltransferase5-enolpyruvylshikimate-3-phosphate
The seven enzymes involved in the shikimate pathway are DAHP synthase, 3-dehydroquinate synthase, 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase.
Thus, the two substrates of this enzyme are phosphoenolpyruvate (PEP) and 3-phospho-shikimate, whereas its two products are phosphate and 5-enolpyruvylshikimate-3-phosphate.

Cyclohexanecarboxylic acid

cyclohexanecarboxylic acids
Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid.
shikimic acid

Tryptophan

Trptryptophan metabolism L -tryptophan
The shikimate pathway is a seven step metabolic route used by bacteria, fungi, algae, parasites, and plants for the biosynthesis of aromatic amino acids (phenylalanine, tyrosine, and tryptophan). indole, indole derivatives and aromatic amino acid tryptophan and tryptophan derivatives such as the psychedelic compound dimethyltryptamine
Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate: anthranilate condenses with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate as a by-product.

Aminoshikimic acid

Aminoshikimic acid is also an alternative to shikimic acid as a starting material for the synthesis of oseltamivir.
Aminoshikimic acid is also an alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir (Tamiflu).

Glyphosate

Roundupglycosphateglyphosates
Glyphosate, the active ingredient in the herbicide Roundup, kills plants by interfering with the shikimate pathway in plants.
It blocks this pathway by inhibiting the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS), which catalyzes the reaction of shikimate-3-phosphate (S3P) and phosphoenolpyruvate to form 5-enolpyruvyl-shikimate-3-phosphate (EPSP).

Chorismic acid

chorismate
Prephenic acid is then synthesized by a Claisen rearrangement of chorismate by Chorismate mutase. The pathway starts with two substrates, phosphoenol pyruvate and erythrose-4-phosphate and ends with chorismate, a substrate for the three aromatic amino acids.
Shikimate → shikimate-3-phosphate → 5-enolpyruvylshikimate-3-phosphate (5-O-(1-carboxyvinyl)-3-phosphoshikimate)

Fiddlehead fern

fiddleheadfiddleheadskasrod
Nevertheless, it is recommended to roast tree fern fronds, a specialty called fiddlehead (furled fronds of a young tree fern in the order Cyatheales, harvested for use as a vegetable).
It is recommended to fully cook fiddleheads to destroy the shikimic acid.

N,N-Dimethyltryptamine

DMTdimethyltryptamineN'',''N''-dimethyltryptamine
indole, indole derivatives and aromatic amino acid tryptophan and tryptophan derivatives such as the psychedelic compound dimethyltryptamine
Dimethyltryptamine is an indole alkaloid derived from the shikimate pathway.

Genetically modified crops

genetically modifiedtransgenic cropsgenetically modified crop
"Roundup Ready" genetically modified crops overcome that inhibition.
Glyphosate (the active ingredient in Roundup and other herbicide products) kills plants by interfering with the shikimate pathway in plants, which is essential for the synthesis of the aromatic amino acids phenylalanine, tyrosine, and tryptophan.