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Chorismic acid





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(Redirected from Chorismate)
 


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

  • 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.
  • Chorismic acid
    Chemical structure of chorismic acid
    Names
    IUPAC name

    (3R,4R)-3-[(1-carboxyvinyl)oxy]-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=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 checkY

      Key: WTFXTQVDAKGDEY-HTQZYQBOSA-N checkY

    • 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

    Chemical formula

    C10H10O6
    Molar mass 226.184 g·mol−1
    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 [77 °F], 100 kPa).

    checkY verify (what is checkY☒N ?)

    Infobox references

    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

    edit

    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

    edit

    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

    edit

    References

    edit
    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.
  • ^ 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.
  • edit

    Retrieved from "https://en.wikipedia.org/w/index.php?title=Chorismic_acid&oldid=1141248121"
     



    Last edited on 24 February 2023, at 03:05  





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    This page was last edited on 24 February 2023, at 03:05 (UTC).

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