Département de chimie moléculaire

Oxinobactin I (R = 8-HO-7-quinolinyl), an analog of the sideophore enterobactin I [R = 2,3-(HO)2C6H3], is prepd. from L-serine Me ester and 8-hydroxy-7-quinolinecarboxylic acid. Tritylation of L-serine Me ester, chemoselective condensation to the triaminotrilactone, and hydrolysis of the trityl groups yields the macrocyclic triaminotrilactone trihydrochloride, while esterification of 8-hydroxy-7-quinolinecarboxylic acid, benzylation, ester hydrolysis, and reaction with cyanuric trifluoride yields 8-(benzyloxy)-7-quinolinecarbonyl fluoride; reaction of the trilactone with the acyl fluoride followed by hydrogenolysis of the benzyl groups under iron-free conditions provides I (R = 8-HO-7-quinolinyl). The complexation of iron by I [R = 8-HO-7-quinolinyl, 2,3-(HO)2C6H3] are compared; oxinobactin is as effective as enterobactin for the complexation of FeIII at physiol. pH but has improved complexing ability at acidic pH. [on SciFinder(R)]