(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
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.[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

  1. ^ Davies GM, Barrett-Bee KJ, Jude DA, Lehan M, Nichols WW, Pinder PE, Thain JL, Watkins WJ, Wilson RG (1994). "(6S)-6-Fluoroshikimic Acid, an Antibacterial Agent Acting on the Aromatic Biosynthetic Pathway". Antimicrobial Agents and Chemotherapy. 38 (2): 403–406. doi:10.1128/AAC.38.2.403. PMC 284469. PMID 8192477.
  2. ^ McConkey GA (1999). "Targeting the Shikimate Pathway in the Malaria Parasite Plasmodium falciparum". Antimicrobial Agents and Chemotherapy. 43 (1): 175–177. doi:10.1128/AAC.43.1.175. PMC 89043. PMID 9869588.
  3. ^ Bornemann S, Ramjee MK, Balasubramanian S, Abell C, Coggins JR, Lowe DJ, Thorneley RN (1995). "Escherichia coli Chorismate Synthase Catalyzes the Conversion of (6S)-6-Fluoro-5-enolpyruvylshikimate-3-phosphate to 6-Fluorochorismate". Journal of Biological Chemistry. 270 (39): 22811–22815. doi:10.1074/jbc.270.39.22811. PMID 7559411.
  4. ^ Ewart CD, Jude DA, Thain JL, Nichols WW (1995). "Frequency and Mechanism of Resistance to Antibacterial Action of ZM 240401, (6S)-6-Fluoro-Shikimic Acid". Antimicrobial Agents and Chemotherapy. 39 (1): 87–93. doi:10.1128/AAC.39.1.87. PMC 162490. PMID 7695335.
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