Synthesis of a 2-indolylphosphonamide derivative with inhibitory activity against yersiniabactin biosynthesis

We report the synthesis of an adenosyl-derived indolylphosphonamide analogue of salicyladenosylmonophosphate involved in the plague and tuberculosis siderophore biosyntheses. The compound proved to be a potent inhibitor of the Yersinia pestis salicylate adenylation domain YbtE catalyzing the initial step of yersiniabactin biosynthesis.