(6S)-6-Fluoroshikimic acid

(6S)-6-Fluoroshikimic acid (6S)-6-Fluoroshikimic acid.svg 150px Chemical structure of (6S)-6-fluoroshikimic acid (3R,4R,5S,6S)-6-Fluoro-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid changed ChemSpider 133398-72-8 correct FDA 48P26AK8X8 10219767 8395259 F[C@H]1C(=C/[C@@H](O)[C@@H](O)[C@@H]1O)\C(=O)O 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 XFSMSJCDVCOESF-JGWLITMVBO 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 XFSMSJCDVCOESF-JGWLITMVSA-N C7H9FO5 192.14 g/mol (6S)-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway. (6S)-6-Fluoroshikimic Acid, an Antibacterial Agent Acting on the Aromatic Biosynthetic Pathway Davies GM, Barrett-Bee KJ, Jude DA, Lehan M, Nichols WW, Pinder PE, Thain JL, Watkins WJ, Wilson RG Antimicrobial Agents and Chemotherapy 1994 38 2 403–406 8192477 10.1128/AAC.38.2.403 284469 It may be used against Plasmodium falciparum, the causative agent of malaria. McConkey GA Targeting the Shikimate Pathway in the Malaria Parasite Plasmodium falciparum Antimicrobial Agents and Chemotherapy 1999 43 1 175–177 9869588 89043 10.1128/AAC.43.1.175 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.Bornemann S, Ramjee MK, Balasubramanian S, Abell C, Coggins JR, Lowe DJ, Thorneley RN Escherichia coli Chorismate Synthase Catalyzes the Conversion of (6S)-6-Fluoro-5-enolpyruvylshikimate-3-phosphate to 6-Fluorochorismate Journal of Biological Chemistry 1995 270 39 22811–22815 10.1074/jbc.270.39.22811 7559411 free The use of the molecule led to resistances in Escherichia coli. Frequency and Mechanism of Resistance to Antibacterial Action of ZM 240401, (6S)-6-Fluoro-Shikimic Acid Ewart CD, Jude DA, Thain JL, Nichols WW Antimicrobial Agents and Chemotherapy 1995 39 1 87–93 10.1128/AAC.39.1.87 7695335 162490 See also Shikimic acid References Category:Antibiotics Category:Fluorinated carboxylic acids Category:Cyclitols Category:Halohydrins Category:Cyclohexenes