1-(Dihydroxyphosphynyl)vinyl phosphate: The phosphonate analogue of phosphoenolpyruvate is a pH-dependent substrate of Kdo8P synthase

The phosphonate analogue of PEP (structure 5), in which the carboxylate group is replaced by an isosteric phosphonate, was synthesized and evaluated as a substrate and as an inhibitor of the Kdo8P synthase. It was demonstrated that 5 is a very slow, pH-dependent substrate of the enzyme.