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Aminoshikimic acid

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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
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: GSAKPGCLECHWSP-PBXRRBTRSA-N
  • 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/s1Key: GSAKPGCLECHWSP-PBXRRBTRBE
SMILES
  • O=C(O)/C1=C/(O)(O)(N)C1
Properties
Chemical formula C7H11NO4
Molar mass 173.168 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) 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. The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.

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. 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."
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