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Revision as of 12:35, 29 November 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 14:04, 18 June 2024 edit undoMicromesistius (talk | contribs)Autopatrolled, Extended confirmed users37,469 edits fix link 
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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 399507038 | verifiedrevid = 399508433
| ImageFileL1 = Aminoshikimic acid.png | ImageFileL1 = Aminoshikimic acid.png
| ImageSizeL1 = 125px | ImageSizeL1 = 125px
| ImageFileR1 = Aminoshikimic-acid-3D-balls.png | ImageFileR1 = Aminoshikimic-acid-3D-balls.png
| ImageSizeR1 = 125px | ImageSizeR1 = 125px
| IUPACName = (3''R'',4''S'',5''R'')-5-Amino-3,4-dihydroxycyclohex-1-enecarboxylic acid | PIN = (3''R'',4''S'',5''R'')-5-Amino-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
| OtherNames = Aminoshikimate | OtherNames = Aminoshikimate
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChIKey = GSAKPGCLECHWSP-PBXRRBTRBE | InChIKey = GSAKPGCLECHWSP-PBXRRBTRBE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GSAKPGCLECHWSP-PBXRRBTRSA-N | StdInChIKey = GSAKPGCLECHWSP-PBXRRBTRSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 178948-66-8 | CASNo = 178948-66-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 74Z3GVA58B
| PubChem = 443636 | PubChem = 443636
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| InChI = 1/C7H11NO4/c8-4-1-3(7(11)12)2-5(9)6(4)10/h2,4-6,9-10H,1,8H2,(H,11,12)/t4-,5-,6+/m1/s1 | InChI = 1/C7H11NO4/c8-4-1-3(7(11)12)2-5(9)6(4)10/h2,4-6,9-10H,1,8H2,(H,11,12)/t4-,5-,6+/m1/s1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=7|H=11|N=1|O=4 | C=7 | H=11 | N=1 | O=4
| Appearance = | Appearance =
| Density = | Density =
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| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
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==History== ==History==
Aminoshikimic acid is an unnatural carbohydrate, although aminoshikimic acid is the namesake of the ], which generates the 3-amino-5-hydroxybenzoic acid (AHBA) starter unit required for the biosynthesis of the ]s and ]s.<ref>{{cite journal| doi= 10.1039/np9971400433| author= Floss, H. G. Aminoshikimic acid is an unnatural carbohydrate, although aminoshikimic acid is the namesake of the ], which generates the 3-amino-5-hydroxybenzoic acid (AHBA) starter unit required for the biosynthesis of the ]s and ]s.<ref>{{cite journal| doi= 10.1039/np9971400433| author= Floss, H. G.
| title = Natural products derived from unusual variants of the shikimate pathway. | title = Natural products derived from unusual variants of the shikimate pathway
| journal = Nat Prod Rep. | journal = Natural Product Reports
| year = 1997 | year = 1997
| volume = 14 | volume = 14
| pages = 433–452 | pages = 433–452
| url = http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400433| pmid= 9364776| issue= 5 | pmid= 9364776| issue= 5
}}</ref> The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.<ref>{{cite journal| author= Guo, Jiantao; Frost, John }}</ref> The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.<ref>{{cite journal|author1=Guo, Jiantao |author2=Frost, John | title = Synthesis of aminoshikimic acid
| journal = Organic Letters
| title = Synthesis of Aminoshikimic Acid
| journal = Org. Lett.
| year = 2004 | year = 2004
| volume = 6 | volume = 6
| pages = 1585–1588 | pages = 1585–1588
| url = http://pubs.acs.org/doi/abs/10.1021/ol049666e| doi= 10.1021/ol049666e| pmid= 15128242| issue= 10 | doi= 10.1021/ol049666e| pmid= 15128242| issue= 10
}}</ref> }}</ref>


==Pharmaceutical uses== ==Pharmaceutical uses==
Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir.<ref>{{cite journal| author= Frost, J. and Guo, J. Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir.<ref>Frost, John & Jiantao Guo. {{patent |US |20070190621A1 |"Synthesis of oseltamivir carboxylates."}}</ref> Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals. As with shikimic acid, aminoshikimic acid is an attractive candidate for use as the core scaffold for synthesis of combinatorial libraries.
| title = Synthesis of oseltamivir carboxylates, US patent 2007/0190621 A1
| year = 2007
| url = http://www.google.com/patents?id=ZCeBAAAAEBAJ&dq=%22Synthesis+of+oseltamivir+carboxylates%22
}}</ref> Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals. As with shikimic acid, aminoshikimic acid is an attractive candidate for use as the core scaffold for synthesis of combinatorial libraries.


==References== ==References==
{{reflist}} {{reflist}}


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