Chorismic acid

Chorismic acid

IUPAC name (3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
CAS number	617-12-9^Y
ChemSpider	11542^Y
ChEBI	CHEBI:17333^Y
Jmol-3D images	Image 1
SMILES O=C(O)C1=C/[C@@H](O/C(C(=O)O)=C)[C@H](O)/C=C1
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^Y Key: WTFXTQVDAKGDEY-HTQZYQBOSA-N^Y 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
Properties
Molecular formula	C₁₀H₁₀O₆
Molar mass	226.18 g mol⁻¹
Melting point	140 °C, 413 K, 284 °F
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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 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 → chorismate.

External links

Shikimate and chorismate biosynthesis

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. http://www.nature.com/nature/journal/v414/n6863/full/414562a.html.
^ Henry George Liddell, Robert Scott, Henry Stuart Jones and Roderick McKenzie. 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. edit