Chorismic acid

Chorismic acid
Names
	IUPAC name (3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
CAS Number	617-12-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17333 ;
ChemSpider	11542 ;
ECHA InfoCard	100.164.204
PubChem CID	12039;
UNII	GI1BLY82Y1;
	InChI InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1 Key: WTFXTQVDAKGDEY-HTQZYQBOSA-N ; InChI=1/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1 Key: WTFXTQVDAKGDEY-HTQZYQBOBD;
	SMILES O=C(O)C1=C/[C@@H](O/C(C(=O)O)=C)[C@H](O)/C=C1;
Properties
Chemical formula	C10H10O6
Molar mass	226.18 g·mol−1
Melting point	140 °C (284 °F; 413 K)
Hazards
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H302, H312, H315, H319, H332, H335, H350, H361
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P280, P281, P301+312, P302+352, P304+312, P304+340, P305+351+338, P308+313, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for:

The aromatic amino acids phenylalanine, tryptophan, and tyrosine
Indole, indole derivatives and tryptophan
2,3-Dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis
The plant hormone salicylic acid^[1]
Many alkaloids and other aromatic metabolites.
The folate precursor para-aminobenzoate (pABA)
The biosynthesis of Vitamin K and folate in plants and microorganisms.

The name chorismic acid derives from a classical Greek word, χωρίζω meaning "to separate",^[2] because the compound plays a role as a branch-point in aromatic amino acid biosynthesis.^[3]

Biosynthesis

Shikimate → shikimate-3-phosphate → 5-enolpyruvylshikimate-3-phosphate (5-O-(1-carboxyvinyl)-3-phosphoshikimate)

Chorismate synthase is an enzyme that catalyzes the final chemical reaction 5-O-(1-carboxyvinyl)-3-phosphoshikimate → chorismate + phosphate.

Metabolism

Chorismate is transformed into para-aminobenzoic acid by the enzymes 4-amino-4-deoxychorismate synthase and 4-amino-4-deoxychorismate lyase.

Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria.

References

↑ Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid for plant defence". Nature. 414 (6863): 562–5. doi:10.1038/35107108. PMID 11734859.
↑ Henry George Liddell; Robert Scott; Henry Stuart Jones & Roderick McKenzie. A Greek-English Lexicon. ISBN 0-19-864226-1.
↑ Gibson, F. (1999). "The elusive branch-point compound of aromatic amino acid biosynthesis". Trends in Biochemical Sciences. 24 (1): 36–38. doi:10.1016/S0968-0004(98)01330-9. PMID 10087921.

External links

Shikimate and chorismate biosynthesis

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[1] Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid for plant defence". Nature. 414 (6863): 562–5. doi:10.1038/35107108. PMID 11734859.

[2] Henry George Liddell; Robert Scott; Henry Stuart Jones & Roderick McKenzie. A Greek-English Lexicon. ISBN 0-19-864226-1.

[3] Gibson, F. (1999). "The elusive branch-point compound of aromatic amino acid biosynthesis". Trends in Biochemical Sciences. 24 (1): 36–38. doi:10.1016/S0968-0004(98)01330-9. PMID 10087921.