Aerobactin

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

Aerobactin

Names
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 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]

Other homologs

• Rhizobactin from Sinorhizobium[6]
• Alcaligin from Bordetella[6]

References

1. J. B. Neilands (1995). "Siderophores: Structure and Function of Microbial Iron Transport Compounds". J. Biol. Chem. 270 (45): 26723–26726. doi:10.1074/jbc.270.45.26723. PMID 7592901.
2. Johnson JR, Moseley SL, Roberts PL, Stamm WE (February 1988). "Aerobactin and other virulence factor genes among strains of Escherichia coli causing urosepsis: association with patient characteristics". Infect. Immun. 56 (2): 405–12. doi:10.1128/iai.56.2.405-412.1988. PMC 259296. PMID 2892793.
3. Meyrier A (1999). "Urinary Tract Infection". In Schrier RW, Cohen AH, Glassock RJ, Grünfeld JP (eds.). Atlas of diseases of the kidney (PDF). 2. Oxford: Blackwell Science. ISBN 0-632-04387-3.
4. de Lorenzo V, Bindereif A, Paw BH, Neilands JB (February 1986). "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. doi:10.1128/jb.165.2.570-578.1986. PMC 214457. PMID 2935523.
5. Forman S, Nagiec MJ, Abney J, Perry RD, Fetherston JD (July 2007). "Analysis of the aerobactin and ferric hydroxamate uptake systems of Yersinia pestis". Microbiology. 153 (Pt 7): 2332–41. doi:10.1099/mic.0.2006/004275-0. PMID 17600077.
6. Cianciotto NP (June 2007). "Iron acquisition by Legionella pneumophila". Biometals. 20 (3–4): 323–31. doi:10.1007/s10534-006-9057-4. PMID 17180462.