Irreversible inhibition of type I dehydroquinase by substrates for type II dehydroquinase.
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.
Bello
C G
CG
Cambridge Centre for Molecular Recognition, University Chemical Laboratory, UK.
Harris
J M
JM
Manthey
M K
MK
Coggins
J R
JR
Abell
C
C
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
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