2.02012-07-30 14:55:20 -06002015-06-03 17:21:11 -0600ECMDB21333M2MDB001734FerroxamineFerroxamine is a member of the chemical class known as Hydroxamic Acids. These are compounds containing an hydroxamic acid functional group in which an hydroxylamine is inserted into a carboxylic acid. Its general structure is R-CO-NH-OH, with an R as an organic residue. Ferrioxamine is catalyzed by fhuF. The phenotype of fhuF mutants and the structural features of the FhuF protein suggest that FhuF is involved in the reduction of ferric iron in cytoplasmic ferrioxamine B. (PMID 9990318) Insertional inactivation and gene replacement of both genes showed that while FhuD2 is involved in the transport of iron(III) in complex with ferrichrome, ferrioxamine B, aerobactin, and coprogen. FhuD1 shows a more limited substrate range, capable of only iron(III)-ferrichrome and iron(III)-ferrioxamine B transport in S. (PMID 11489851) Removal of iron from coprogen, ferrichrome, and ferrioxamine B was significantly lower in fhuF mutants compared to the corresponding parental strains, which suggested that FhuF is involved in iron removal from these hydroxamate-type siderophores. (PMID 14756576)Desferal-iron(III)FerrioxamineC25H45FeN6O8613.505613.26482957914836-73-8[Fe+3].CC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCNInChI=1S/C25H45N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h2-20,26H2,1H3,(H,27,33)(H,28,34);/q-3;+3SRMBQCVUAVULDJ-UHFFFAOYSA-NCytosolExtra-organismPeriplasmlogp1.17logs-3.15solubility4.35e-01 g/lpka_strongest_acidic13.79pka_strongest_basic9.61average_mass613.505mono_mass613.264829579smiles[Fe+3].CC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCN=C(O)CCC(=O)N([O-])CCCCCNformulaC25H45FeN6O8inchiInChI=1S/C25H45N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h2-20,26H2,1H3,(H,27,33)(H,28,34);/q-3;+3inchikeySRMBQCVUAVULDJ-UHFFFAOYSA-Npolar_surface_area224.05polarizability61.65acceptor_count12donor_count3physiological_charge1formal_charge0Specdb::CMs1088494Specdb::EiMs2109Specdb::MsMs1294417Specdb::MsMs1294418Specdb::MsMs1294419Specdb::MsMs1409077Specdb::MsMs1409078Specdb::MsMs1409079Specdb::MsMs2467499Specdb::MsMs2467500Specdb::MsMs2467501Specdb::MsMs2498645Specdb::MsMs2498646Specdb::MsMs2498647123851110391C07597CPD0-2124Matzanke, B. F., Anemuller, S., Schunemann, V., Trautwein, A. X., Hantke, K. (2004). "FhuF, part of a siderophore-reductase system." Biochemistry 43:1386-1392.14756576Sebulsky, M. T., Heinrichs, D. E. (2001). "Identification and characterization of fhuD1 and fhuD2, two genes involved in iron-hydroxamate uptake in Staphylococcus aureus." J Bacteriol 183:4994-5000.11489851Iron(3+)-hydroxamate import ATP-binding protein fhuCP07821FHUC_ECOLIfhuChttp://ecmdb.ca/proteins/P07821.xmlFerric iron reductase protein fhuFP39405FHUF_ECOLIfhuFhttp://ecmdb.ca/proteins/P39405.xmlIron(3+)-hydroxamate import system permease protein fhuBP06972FHUB_ECOLIfhuBhttp://ecmdb.ca/proteins/P06972.xmlIron(3+)-hydroxamate-binding protein fhuDP07822FHUD_ECOLIfhuDhttp://ecmdb.ca/proteins/P07822.xmlIron(3+)-hydroxamate import ATP-binding protein fhuCP07821FHUC_ECOLIfhuChttp://ecmdb.ca/proteins/P07821.xmlIron(3+)-hydroxamate import system permease protein fhuBP06972FHUB_ECOLIfhuBhttp://ecmdb.ca/proteins/P06972.xmlFerrichrome-iron receptorP06971FHUA_ECOLIfhuAhttp://ecmdb.ca/proteins/P06971.xmlBiopolymer transport protein exbBP0ABU7EXBB_ECOLIexbBhttp://ecmdb.ca/proteins/P0ABU7.xmlBiopolymer transport protein exbDP0ABV2EXBD_ECOLIexbDhttp://ecmdb.ca/proteins/P0ABV2.xmlProtein tonBP02929TONB_ECOLItonBhttp://ecmdb.ca/proteins/P02929.xmlIron(3+)-hydroxamate-binding protein fhuDP07822FHUD_ECOLIfhuDhttp://ecmdb.ca/proteins/P07822.xmlAdenosine triphosphate + Water + Ferroxamine > ADP + Ferroxamine + Hydrogen ion + PhosphateAdenosine triphosphate + Water + Ferroxamine > ADP + Ferroxamine + Hydrogen ion + PhosphateFADH2 + 2 Ferroxamine > FAD +2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion2 Ferroxamine + FMNH >2 Iron +2 ferroxamine minus Fe(3) + Flavin Mononucleotide +2 Hydrogen ion2 Ferroxamine + Reduced riboflavin >2 Iron +2 ferroxamine minus Fe(3) +2 Hydrogen ion + RiboflavinFe3+ + ferroxamine minus Fe(3) > Ferroxamine