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 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17333 Y
ChemSpider	11542 Y
ECHA InfoCard	100.164.204
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
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
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 name chorismic acid derives from a classical Greek word, χωρίζω meaning "to separate", because the compound plays a role as a branch-point in aromatic amino acid 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.

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.