Aminoshikimic acid

Aminoshikimic acid
Names
Preferred IUPAC name
(3R,4S,5R)-5-Amino-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
Other names
Aminoshikimate
Identifiers
CAS Number
  • 178948-66-8 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 391778 checkY
PubChem CID
  • 443636
UNII
  • 74Z3GVA58B checkY
CompTox Dashboard (EPA)
  • DTXSID70332123 Edit this at Wikidata
InChI
  • InChI=1S/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 checkY
    Key: GSAKPGCLECHWSP-PBXRRBTRSA-N checkY
  • 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
    Key: GSAKPGCLECHWSP-PBXRRBTRBE
  • O=C(O)/C1=C/[C@@H](O)[C@@H](O)[C@H](N)C1
Properties
Chemical formula
 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).
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Infobox references
Chemical compound

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).

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 ansamycins and mitomycins.[1] The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.[2]

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.[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.

References

  1. ^ Floss, H. G. (1997). "Natural products derived from unusual variants of the shikimate pathway". Natural Product Reports. 14 (5): 433–452. doi:10.1039/np9971400433. PMID 9364776.
  2. ^ Guo, Jiantao; Frost, John (2004). "Synthesis of aminoshikimic acid". Organic Letters. 6 (10): 1585–1588. doi:10.1021/ol049666e. PMID 15128242.
  3. ^ Frost, John & Jiantao Guo. US 20070190621A1  "Synthesis of oseltamivir carboxylates."