(6S)-6-Fluoroshikimic acid

(6S)-6-Fluoroshikimic acid

Names
IUPAC name (3R,4R,5S,6S)-6-fluoro-3,4,5-trihydroxycyclohexene-1-carboxylic acid
Identifiers
ChemSpider	8395259
Jmol interactive 3D	Image
PubChem	10219767
InChI 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
SMILES F[C@H]1C(=C/[C@@H](O)[C@@H](O)[C@@H]1O)\C(=O)O
Properties
Chemical formula	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

• Shikimic acid

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" (pdf). 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" (pdf). Antimicrobial Agents and Chemotherapy 43 (1): 175–177. 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" (pdf). 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" (pdf). Antimicrobial Agents and Chemotherapy 39 (1): 87–93. doi:10.1128/AAC.39.1.87. PMC 162490. PMID 7695335.