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{{chembox |
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{{chembox |
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| verifiedrevid = 446302468 |
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| verifiedrevid = 446340913 |
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| Name = Chorismic acid |
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| Name = Chorismic acid |
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| ImageFile = Chorismic acid.svg |
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| ImageFile = Chorismic acid.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageName = Chemical structure of chorismic acid |
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| ImageName = Chemical structure of chorismic acid |
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| ImageFile1 = Chorismic-acid-from-xtal-3D-bs-17.png |
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| IUPACName = (3''R'',4''R'')-3--4-hydroxycyclohexa-1,5-diene-1-carboxylic acid |
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| IUPACName = (3''R'',4''R'')-3--4-hydroxycyclohexa-1,5-diene-1-carboxylic acid |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17333 |
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| ChEBI = 17333 |
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| PubChem = 12039 |
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| UNII = GI1BLY82Y1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| C=10|H=10|O=6 |
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| C=10|H=10|O=6 |
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| MeltingPtC = 140 |
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| MeltingPtC = 140 |
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}} |
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| Section8 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|302|312|315|319|332|335|350|361}} |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+312|304+340|305+351+338|308+313|312|321|322|330|332+313|337+313|362|363|403+233|405|501}} |
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}} |
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'''Chorismic acid''', more commonly known as its ] form '''chorismate''', is an important biochemical intermediate in plants and microorganisms. It is a precursor for: |
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'''Chorismic acid''', more commonly known as its ] form '''chorismate''', is an important biochemical intermediate in plants and microorganisms. It is a precursor for: |
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* The aromatic ]s ] and ] |
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* The aromatic ]s ], ], and ] |
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* ], indole derivatives and ] |
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* ], indole derivatives and ] |
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* ] (DHB) used for ] biosynthesis |
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* ] (DHB) used for ] biosynthesis |
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* The ] ]<ref>{{cite journal |author=Wildermuth MC, Dewdney J, Wu G, Ausubel FM |
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* The ] ]<ref>{{cite journal |vauthors=Wildermuth MC, Dewdney J, Wu G, Ausubel FM |
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|title=Isochorismate synthase is required to synthesize salicylic acid for plant defence |
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|title=Isochorismate synthase is required to synthesize salicylic acid for plant defence |
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|journal= Nature |
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|journal= Nature |
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|pmid= 11734859 |
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|pmid= 11734859 |
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|doi =10.1038/35107108 |
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|doi =10.1038/35107108 |
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|bibcode=2001Natur.414..562W |
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|url=http://www.nature.com/nature/journal/v414/n6863/full/414562a.html}}</ref> |
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}}</ref> |
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* Many ]s and other aromatic ]s. |
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* Many ]s and other aromatic ]s. |
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*The folate precursor ''para''-aminobenzoate ] |
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* The biosynthesis of ] and ] in plants and microorganisms. |
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The name chorismic acid derives from a classical greek word, ''χωρίζω'' meaning "to separate",<ref>{{cite book|isbn=0-19-864226-1|name=]|authors=Henry George Liddell, Robert Scott, Henry Stuart Jones and Roderick McKenzie}}</ref> because the compound plays a role as a branch-point in aromatic amino acid biosynthesis.<ref>{{Cite doi|10.1016/S0968-0004(98)01330-9}}</ref> |
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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> |
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==Biosynthesis== |
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== Biosynthesis == |
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] → shikimate-3-phosphate → 5-enolpyruvylshikimate-3-phosphate → chorismate. |
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] → shikimate-3-phosphate → 5-enolpyruvylshikimate-3-phosphate (5-''O''-(1-carboxyvinyl)-3-phosphoshikimate) |
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:] |
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:] |
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] is an enzyme that catalyzes the final chemical reaction: |
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:] → chorismate + phosphate. |
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:] |
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== Metabolism == |
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:] |
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Chorismate is transformed into ''para''-aminobenzoic acid by the enzymes ] and ]. |
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] is an enzyme that transforms chorismate into ] and ]. This enzyme catalyses the first step in ] biosynthesis in '']'' and other Gram-negative bacteria. |
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==External links== |
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==References== |
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==See also== |
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* ] |
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* ] |
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== References == |
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<references/> |
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<references/> |
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== External links == |
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