Inhibition of chorismate mutase activity of chorismate mutase-prephenate dehydrogenase from Aerobacter aerogenes

Inhibition data (I50 values) have been obtained for inhibitors of the chorismate mutase activity of chorismate mutase-prephenate dehydrogenase from Aerobacter aerogenes. Several 1-substituted adamantane derivatives were investigated; the order of decreasing inhibitory activity with the various substituents was -PO32- much greater than -P(OCH3)O2- greater than -CO2- greater than -CH2CO2- greater than -SO2- greater than SO3-. 3-Chloroadamantane-1-acetic acid was slightly less effective than adamantane-1-acetic acid. 2-(1-Carboxy-1,4-dihydrobenzyl)acrylic acid (19), an analogue of prephenate, was an effective inhibitor. Other substances investigated, including 2,4,10-trioxaadamantane-1-acetic acid (15), 5-enolpyruvylshikimic acid (20), and 1-(carboxyethyl)-1,4-dihydrobenzoic acid (18), failed to inhibit chorismate mutase activity under the conditions investigated.