(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.
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.
Frederickson
Martyn
M
University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1EW.
Roszak
Aleksander W
AW
Coggins
John R
JR
Lapthorn
Adrian J
AJ
Abell
Chris
C
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
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