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 (Scheme 1 and Scheme 2), (2R)-2-fluoro-3-dehydroquinic acid (Scheme 1 and Scheme 2) and 2-bromo-3-dehydroshikimic acid ( 4), all excellent substrates for type II dehydroquinase, are shown to be irreversible inhibitors of type I dehydroquinase.