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Antibiotic
(6S)-6-Fluoroshikimic acid
Другие языки:

    (6S)-6-Fluoroshikimic acid

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    (6S)-6-Fluoroshikimic acid
    Chemical structure of (6S)-6-fluoroshikimic acid
    Names
    Preferred IUPAC name
    (3R,4R,5S,6S)-6-Fluoro-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
    Identifiers
    3D model (JSmol)
    ChemSpider
    PubChem CID
    UNII
    • 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).

    (6S)-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway. It may be used against Plasmodium falciparum, the causative agent of malaria. 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.

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

    See also


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