(6S)-6-Fluoroshikimic acid

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(6S)-6-Fluoroshikimic acid
Chemical structure of (6S)-6-fluoroshikimic acid
Names
IUPAC name
(3R,4R,5S,6S)-6-fluoro-3,4,5-trihydroxycyclohexene-1-carboxylic acid
Identifiers
ChemSpider 8395259
Jmol 3D model Interactive image
PubChem 10219767
  • InChI=1S/C7H9FO5/c8-4-2(7(12)13)1-3(9)5(10)6(4)11/h1,3-6,9-11H,(H,12,13)/t3-,4+,5-,6-/m1/s1
    Key: XFSMSJCDVCOESF-JGWLITMVSA-N
  • InChI=1/C7H9FO5/c8-4-2(7(12)13)1-3(9)5(10)6(4)11/h1,3-6,9-11H,(H,12,13)/t3-,4+,5-,6-/m1/s1
    Key: XFSMSJCDVCOESF-JGWLITMVBO
  • F[C@H]1C(=C/[C@@H](O)[C@@H](O)[C@@H]1O)\C(=O)O
Properties
C7H9FO5
Molar mass 192.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(6S)-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway.[1] It may be used against Plasmodium falciparum, the causative agent of malaria.[2] The molecule is targeting the enzymes of the shikimate pathway. This metabolic pathway is not present in mammals. The mechanism of action of the molecule is not through the inhibition of chorismate synthase but by the inhibition of 4-aminobenzoic acid synthesis.[3]

The use of the molecule led to resistances in Escherichia coli.[4]

See also

References

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  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.

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