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* Many ]s and other aromatic ]s. * Many ]s and other aromatic ]s.
*The folate precursor ''para''-aminobenzoate ] *The folate precursor ''para''-aminobenzoate ]
* The biosynthesis of ] and ] in plants and microorganisms. * The biosynthesis of ] and ] in plants and microorganisms.


The name chorismic acid derives from a classical Greek word {{lang|grc|χωρίζω}} meaning "to separate",<ref>{{cite book|isbn=0-19-864226-1|title=A Greek-English Lexicon|author=Henry George Liddell|author2=Robert Scott|author3=Henry Stuart Jones|author4=Roderick McKenzie|name-list-style=amp|title-link=A Greek-English Lexicon}}</ref> because the compound plays a role as a branch-point in aromatic amino acid biosynthesis.<ref>{{Cite journal | last1 = Gibson | first1 = F. | title = The elusive branch-point compound of aromatic amino acid biosynthesis | doi = 10.1016/S0968-0004(98)01330-9 | journal = Trends in Biochemical Sciences | volume = 24 | issue = 1 | pages = 36–38 | year = 1999 | pmid = 10087921}}</ref> The name chorismic acid derives from a classical Greek word {{lang|grc|χωρίζω}} meaning "to separate",<ref>{{cite book|isbn=0-19-864226-1|title=A Greek-English Lexicon|author=Henry George Liddell|author2=Robert Scott|author3=Henry Stuart Jones|author4=Roderick McKenzie|name-list-style=amp|title-link=A Greek-English Lexicon}}</ref> because the compound plays a role as a branch-point in aromatic amino acid biosynthesis.<ref>{{Cite journal | last1 = Gibson | first1 = F. | title = The elusive branch-point compound of aromatic amino acid biosynthesis | doi = 10.1016/S0968-0004(98)01330-9 | journal = Trends in Biochemical Sciences | volume = 24 | issue = 1 | pages = 36–38 | year = 1999 | pmid = 10087921}}</ref>

Latest revision as of 03:05, 24 February 2023

Chorismic acid
Chemical structure of chorismic acid
Names
IUPAC name (3R,4R)-3--4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.164.204 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: WTFXTQVDAKGDEY-HTQZYQBOBD
SMILES
  • O=C(O)C1=C/(O/C(C(=O)O)=C)(O)/C=C1
Properties
Chemical formula C10H10O6
Molar mass 226.184 g·mol
Melting point 140 °C (284 °F; 413 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H302, H312, H315, H319, H332, H335, H350, H361
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

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. 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.

External links

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