Aminoshikimic acid: Difference between revisions

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 {{Chembox
+| Watchedfields = changed
-| verifiedrevid = 399507038
+| verifiedrevid =
 | ImageFileL1 = Aminoshikimic acid.png
 | ImageSizeL1 = 125px
 | ImageFileR1 = Aminoshikimic-acid-3D-balls.png
 | ImageSizeR1 = 125px
-| IUPACName = (3''R'',4''S'',5''R'')-5-Amino-3,4-dihydroxycyclohex-1-enecarboxylic acid
+|  = (3''R'',4''S'',5''R'')-5-Amino-3,4-dihydroxycyclohex-1- acid
 | OtherNames = Aminoshikimate
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
 | InChIKey = GSAKPGCLECHWSP-PBXRRBTRBE
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
@@ Line 13: / Line 14: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = GSAKPGCLECHWSP-PBXRRBTRSA-N
+| CASNo_Ref = {{cascite|correct|??}}
 | CASNo = 178948-66-8
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 74Z3GVA58B
 | PubChem = 443636
 | 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
 }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
 | C=7|H=11|N=1|O=4
 | Appearance =
 | Density =
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 | Solubility =
 }}
-| Section3 = {{Chembox Hazards
+|Section3={{Chembox Hazards
 | MainHazards =
 | FlashPt =
-| Autoignition =
+|  =
 }}
 }}
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 ==History==
 Aminoshikimic acid is an unnatural carbohydrate, although aminoshikimic acid is the namesake of the [[aminoshikimate pathway]], which generates the 3-amino-5-hydroxybenzoic acid (AHBA) starter unit required for the biosynthesis of the [[ansamycin]]s and [[mitomycin]]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 =
  | year = 1997
  | volume = 14
  | 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|=Guo, Jiantao Frost, John
+ | journal =
- | title = Synthesis of Aminoshikimic Acid
- | journal = Org. Lett.
  | year = 2004
  | volume = 6
  | 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>
 ==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>{{ |   .  , .
- | 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==
 {{reflist}}
-[[Category:Carboxylic acids]]
+[[Category: acids]]
-[[Category:Diols]]
+[[Category:]]
-[[Category:amines]]
+[[Category:]]
+[[Category:Cyclohexenes]]