Genome mining and chemical analyses revealed that rhizosphere bacteria (Paraburkholderia graminis) produce a new type of siderophore, gramibactin, a lipodepsipeptide that efficiently binds iron with a logβ value of 27.6. Complexation-induced proton NMR chemical shifts show that the unusual N-nitrosohydroxylamine (diazeniumdiolate) moieties participate in metal binding. Gramibactin biosynthesis genes are conserved in numerous plant-associated bacteria associated with rice, wheat, and maize, which may utilize iron from the complex.
Complexes of etifenin (1a), disofenin (1b), and mebrofenin (1c) with GaIII, YIII, and LuIII were synthesized and characterized by NMR spectroscopy and UV/Vis spectroscopy. Stability and protonation constants of the complexes of 1a were determined by potentiometry and distribution diagrams were calculated. It was shown that the YIII and LuIII species are most stable as bis chelates at higher pH, whereas the GaIII complex degrades at pH < 4.5.
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