title: Irreversible inhibition of type I dehydroquinase by substrates for type II dehydroquinase.
abstract: Mechanistic differences between type I and type II dehydroquinases have been exploited in the design of type specific inhibitors. (2R)-2-Bromo-3-dehydroquinic acid (3), (2R)-2-fluoro-3-dehydroquinic acid (5) and 2-bromo-3-dehydroshikimic acid (4), all excellent substrates for type II dehydroquinase, are shown to be irreversible inhibitors of type I dehydroquinase.
authors.affiliation: Cambridge Centre for Molecular Recognition, University Chemical Laboratory, UK.
authors.forename: C G
authors.initials: CG
authors.lastname: Bello
authors.forename: J M
authors.initials: JM
authors.lastname: Harris
authors.forename: M K
authors.initials: MK
authors.lastname: Manthey
authors.forename: J R
authors.initials: JR
authors.lastname: Coggins
authors.forename: C
authors.initials: C
authors.lastname: Abell
mesh_terms: D004791:Enzyme Inhibitors / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D006836:Hydro-Lyases / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D009169:Mycobacterium tuberculosis / Q000201:enzymology; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology
chemical_list: C409803:2-bromo-3-dehydroquinic acid; C409805:2-bromo-3-dehydroshikimic acid; C409804:2-fluoro-3-dehydroquinic acid; D004791:Enzyme Inhibitors; D011801:Quinic Acid; D012765:Shikimic Acid; D006836:Hydro-Lyases; C020000:3-dehydroquinate dehydratase