Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
Aminoshikimic acid is a synthetic crystalline carboxylic acid. It is characterized by multiple stereogenic centers and functional groups arrayed around a six-membered carbocyclic ring. Aminoshikimic acid is also an alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir (Tamiflu).
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
(3R,4S,5R)-5-Amino-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid | |||
Other names
Aminoshikimate | |||
Identifiers | |||
3D model (JSmol) |
|||
ChemSpider | |||
PubChem CID |
|||
UNII | |||
CompTox Dashboard (EPA) |
|||
| |||
| |||
Properties | |||
C7H11NO4 | |||
Molar mass | 173.168 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
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 ansamycins and mitomycins.[1] The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.[2]
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.[3] 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.
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.