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;
	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.^[2] 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]

Other homologs

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

References

↑ 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.
↑ "Aerobactin and other virulence factor genes among strains of Escherichia coli causing urosepsis: association with patient characteristics". Infect. Immun. 56 (2): 405–12. February 1988. doi:10.1128/iai.56.2.405-412.1988. PMID 2892793.
↑ Meyrier A (1999). "Urinary Tract Infection". Atlas of diseases of the kidney. 2. Oxford: Blackwell Science. ISBN 0-632-04387-3. http://www.kidneyatlas.org/book2/adk2_07.pdf.
↑ "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. February 1986. doi:10.1128/jb.165.2.570-578.1986. PMID 2935523.
↑ "Analysis of the aerobactin and ferric hydroxamate uptake systems of Yersinia pestis". Microbiology 153 (Pt 7): 2332–41. July 2007. doi:10.1099/mic.0.2006/004275-0. PMID 17600077.
↑ ^6.0 ^6.1 Cianciotto NP (June 2007). "Iron acquisition by Legionella pneumophila". Biometals 20 (3–4): 323–31. doi:10.1007/s10534-006-9057-4. PMID 17180462.

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[J._B._Neilands-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] "Aerobactin and other virulence factor genes among strains of Escherichia coli causing urosepsis: association with patient characteristics". Infect. Immun. 56 (2): 405–12. February 1988. doi:10.1128/iai.56.2.405-412.1988. PMID 2892793.

[3] Meyrier A (1999). "Urinary Tract Infection". Atlas of diseases of the kidney. 2. Oxford: Blackwell Science. ISBN 0-632-04387-3. http://www.kidneyatlas.org/book2/adk2_07.pdf.

[4] "Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12". J. Bacteriol. 165 (2): 570–8. February 1986. doi:10.1128/jb.165.2.570-578.1986. PMID 2935523.

[5] "Analysis of the aerobactin and ferric hydroxamate uptake systems of Yersinia pestis". Microbiology 153 (Pt 7): 2332–41. July 2007. doi:10.1099/mic.0.2006/004275-0. PMID 17600077.

[Cia07-6] 6.0 ^6.1 Cianciotto NP (June 2007). "Iron acquisition by Legionella pneumophila". Biometals 20 (3–4): 323–31. doi:10.1007/s10534-006-9057-4. PMID 17180462.

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Aerobactin

Topic: Chemistry

Other homologs

References