Aerobactin

Aerobactin
Names
	Preferred IUPAC name (8S,16S)-3,12,21-Trihydroxy-2,10,14,22-tetraoxo-3,9,15,21-tetraazatricosane-8,12,16-tricarboxylic acid
Identifiers
CAS Number	26198-65-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18157;
ChemSpider	110318;
PubChem CID	123762;
CompTox Dashboard (EPA)	DTXSID90904341 ;
	InChI InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 Key: KDHHWXGBNUCREU-HOTGVXAUSA-N; InChI=1/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1 Key: KDHHWXGBNUCREU-HOTGVXAUBP;
	SMILES CC(=O)N(CCCC[C@@H](C(=O)O)NC(=O)CC(CC(=O)N[C@@H](CCCCN(C(=O)C)O)C(=O)O)(C(=O)O)O)O;
Properties
Chemical formula	C22H36N4O13
Molar mass	564.545 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Aerobactin is a bacterial iron chelating agent (siderophore)^[1] found in E. coli and other Enterobacteriaceae species.^[2][1] It is a virulence factor enabling E. coli to sequester iron in iron-poor environments such as the urinary tract.^[3]

Aerobactin is biosynthesized by the oxidation of lysine, catalyzed by the enzyme aerobactin synthase, which is then coupled to citric acid. The gene for this enzyme is found in the aerobactin operon, which is roughly 8 kilobases long and contains 5 or more genes in total.^[4]

Yersinia pestis contains genes relating to aerobactin, but they have been inactivated by a frameshift mutation, thus Y. pestis is no longer able to synthesize aerobactin.^[5]