Chorismic acid

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Chorismic acid
Chemical structure of chorismic acid Chorismic acid.svg
Chemical structure of chorismic acid
Chorismic-acid-from-xtal-3D-bs-17.png
Names
IUPAC name
(3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.164.204 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: WTFXTQVDAKGDEY-HTQZYQBOSA-N Yes check.svgY
  • 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
  • O=C(O)C1=C/[C@@H](O/C(C(=O)O)=C)[C@H](O)/C=C1
Properties
C10H10O6
Molar mass 226.184 g·mol−1
Melting point 140 °C (284 °F; 413 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H302, H312, H315, H319, H332, H335, H350, H361
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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 pathway 1.png

Chorismate synthase is an enzyme that catalyzes the final chemical reaction:

5-O-(1-carboxyvinyl)-3-phosphoshikimate → chorismate + phosphate.
Chorismate pathway 2.png

Metabolism

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

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.[ citation needed ]

See also

References

  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. Bibcode:2001Natur.414..562W. doi:10.1038/35107108. PMID   11734859.
  2. Henry George Liddell; Robert Scott; Henry Stuart Jones & Roderick McKenzie (1996). A Greek-English Lexicon. Clarendon Press. 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.