Agrobactin, a siderophore from Agrobacterium tumefaciens.
A siderophore (microbial iron transport compound) was isolated from low iron cultures of Agrobacterium tumefaciens B6. The substance was characterized as a threonyl peptide of spermidine acylated with 3 residues of 2,3-dihydroxybenzoic acid, the carbonyl group of 1 residue of the latter participating in an oxazoline ring with the beta-hydroxyl of the threonine moiety. The compound, N-[3-(2,3-dihydroxybenzamido)propyl]-N-[4-(2,3-dihydroxybenzamido)butyl]-2-(2,3-dihydroxyphenyl)-trans-5-methyl-oxazoline-4-carboxamide, was given the trivial name agrobactin. Exposure to acid opened the oxazoline ring to afford agrobactin A. Ferric agrobactin A and agrobactin A itself, but not agrobactin or its ferric complex, had some capacity to feed iron to enterobactin-deficient strains of Escherichia coli and Salmonella typhimurium. Agrobactin was produced by A. tumefaciens in response to iron deficiency and was able to reverse the iron starvation in this organism precipitated by the presence of a ferric complexing agent not utilized by the cells.
D001692:Biological Transport; D002396:Catechols / Q000032:analysis* / Q000378:metabolism / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D006863:Hydrogen-Ion Concentration; D007501:Iron / Q000378:metabolism* / Q000494:pharmacology; D010080:Oxazoles / Q000032:analysis / Q000378:metabolism / Q000494:pharmacology; D012231:Rhizobium / Q000032:analysis* / Q000187:drug effects / Q000378:metabolism; D013045:Species Specificity
D002396:Catechols; D010080:Oxazoles; C018813:agrobactin; D007501:Iron