title: (1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases.
abstract: The fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases has been prepared from naturally occurring (-)-quinic acid over seven steps and has been shown to be the most potent inhibitor reported to date of the type II enzyme from Mycobacterium tuberculosis.
authors.affiliation: University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1EW.
authors.forename: Martyn
authors.initials: M
authors.lastname: Frederickson
authors.forename: Aleksander W
authors.initials: AW
authors.lastname: Roszak
authors.forename: John R
authors.initials: JR
authors.lastname: Coggins
authors.forename: Adrian J
authors.initials: AJ
authors.lastname: Lapthorn
authors.forename: Chris
authors.initials: C
authors.lastname: Abell
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D053138:Cyclohexenes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006836:Hydro-Lyases / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000201:enzymology
chemical_list: C488433:3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid; D003509:Cyclohexanecarboxylic Acids; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D006836:Hydro-Lyases; C020000:3-dehydroquinate dehydratase