Vinyl fluoride as an isoelectronic replacement for an enolate anion: inhibition of type II dehydroquinases.
A vinyl fluoride analogue of the intermediate in the reaction catalysed by type II dehydroquinase enzymes has been synthesized over seven steps from (-)-quinic acid and shown to be a potent enzyme inhibitor.
Frederickson
Martyn
M
University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1EW.
Coggins
John R
JR
Abell
Chris
C
D000838:Anions / Q000737:chemistry*; D004563:Electrochemistry; D006836:Hydro-Lyases / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D015394:Molecular Structure; D011801:Quinic Acid / Q000737:chemistry*; D055672:Static Electricity; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000838:Anions; D014753:Vinyl Compounds; D011801:Quinic Acid; C016829:vinyl fluoride; D006836:Hydro-Lyases; C020000:3-dehydroquinate dehydratase