Chorismic acid

Chorismic acid
Chemical structure of 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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.164.204
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 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
C10H10O6
Molar mass 226.184 g·mol−1
Melting point 140 °C (284 °F; 413 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
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).
checkY verify (what is checkYX markN ?)
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",[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 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.[4]

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 (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.
  4. ↑ Basset, G. J.; Quinlivan, E. P.; Ravanel, S.; Rébeillé, F.; Nichols, B. P.; Shinozaki, K.; Seki, M.; Adams-Phillips, L. C.; Giovannoni, J. J.; Gregory JF III; Hanson, A. D. (2004). "Folate synthesis in plants: The p-aminobenzoate branch is initiated by a bifunctional PabA-PabB protein that is targeted to plastids". Proceedings of the National Academy of Sciences of the United States of America. 101 (6): 1496–1501. Bibcode:2004PNAS..101.1496B. doi:10.1073/pnas.0308331100. PMC 341757. PMID 14745019.
This page is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.