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The shikimate pathway (
Then 5-enolpyruvylshikimate-3-phosphate is transformed into chorismate by a chorismate synthase.
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Prephenic acid is then synthesized by a Claisen rearrangement of chorismate by chorismate mutase.
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Prephenate is oxidatively decarboxylated with retention of the 
shikimic acid
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. Its name comes from the Japanese flower ''shik ...
pathway) is a seven-step metabolic pathway
In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell (biology), cell. The reactants, products, and Metabolic intermediate, intermediates of an enzymatic reaction are known as metabolites, which are ...
used by bacteria
Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
, archaea
Archaea ( ) is a Domain (biology), domain of organisms. Traditionally, Archaea only included its Prokaryote, prokaryotic members, but this has since been found to be paraphyletic, as eukaryotes are known to have evolved from archaea. Even thou ...
, fungi
A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...
, alga
Algae ( , ; : alga ) is an informal term for any organisms of a large and diverse group of photosynthetic organisms that are not plants, and includes species from multiple distinct clades. Such organisms range from unicellular microalgae, suc ...
e, some protozoans
Protozoa (: protozoan or protozoon; alternative plural: protozoans) are a polyphyletic group of single-celled eukaryotes, either free-living or parasitic, that feed on organic matter such as other microorganisms or organic debris. Historically ...
, and plant
Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...
s for the biosynthesis
Biosynthesis, i.e., chemical synthesis occurring in biological contexts, is a term most often referring to multi-step, enzyme-Catalysis, catalyzed processes where chemical substances absorbed as nutrients (or previously converted through biosynthe ...
of folate
Folate, also known as vitamin B9 and folacin, is one of the B vitamins. Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and ...
s and aromatic amino acids (tryptophan
Tryptophan (symbol Trp or W)
is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromat ...
, phenylalanine
Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...
, and tyrosine
-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is ...
). This pathway is not found in mammals.
The five enzymes involved in the shikimate pathway are 3-dehydroquinate dehydratase, shikimate dehydrogenase, shikimate kinase, EPSP synthase, and chorismate synthase. In bacteria and eurkaryotes, the pathway starts with two substrates, phosphoenol pyruvate and erythrose-4-phosphate, are processed by DAHP synthase and 3-dehydroquinate synthase to form 3-dehydroquinate. In archaea, 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate synthase condenses L-Aspartic-4-semialdehyde with a sugar to form 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate, which is then turned by 3-dehydroquinate synthase II into 3-dehydroquinate. Both pathways end with chorismate (chrorismic acid), a substrate for the three aromatic amino acids. The fifth enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
involved is the shikimate kinase, an enzyme that catalyzes the ATP-dependent phosphorylation
In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols:
:
This equation can be writ ...
of shikimate
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. Its name comes from the Japanese flower ''shik ...
to form shikimate 3-phosphate (shown in the figure below). Shikimate 3-phosphate is then coupled with phosphoenol pyruvate to give 5-enolpyruvylshikimate-3-phosphate via the enzyme 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase.
Glyphosate, the herbicidal ingredient in Roundup, is a competitive inhibitor of EPSP synthase, acting as a transition state analog
Transition state analogs (transition state analogues), are chemical compounds with a chemical structure that resembles the transition state of a substrate molecule in an enzyme-catalyzed chemical reaction. Enzymes interact with a substrate by mea ...
that binds more tightly to the EPSPS-S3P complex than PEP and inhibits the shikimate pathway.
:
Then 5-enolpyruvylshikimate-3-phosphate is transformed into chorismate by a chorismate synthase.
:
Prephenic acid is then synthesized by a Claisen rearrangement of chorismate by chorismate mutase.
:
Prephenate is oxidatively decarboxylated with retention of the hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
group to give ''p''-hydroxyphenylpyruvate, which is transaminated using glutamate
Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a Essential amino acid, non-essential nutrient for humans, meaning that ...
as the nitrogen source to give tyrosine
-Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is ...
and α-ketoglutarate.
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References
Bibliography
* * * * {{MetabolismMap Metabolic pathways