Chorismic acid

In this article we will delve into the exciting world of Chorismic acid, exploring its origins, its relevance today and its impact on different areas of society. Through a multidisciplinary approach, we will explore the different facets of Chorismic acid, from its influence on popular culture to its application in science and technology. We will immerse ourselves in its history, analyze its implications in the present and glimpse the possible future perspectives it offers. Chorismic acid is a topic that arouses the interest of experts and amateurs alike, and in this article we aim to delve into its complexity, its diversity and its relevance to better understand the world around us.

Chorismic acid
Chemical structure of chorismic acid
Chemical structure of chorismic acid
Names
IUPAC name
(3R,4R)-3--4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.164.204 Edit this at Wikidata
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/(O/C(C(=O)O)=C)(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 , 100 kPa).
checkY verify (what is checkY☒N ?)

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.

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.