Petrobactin

Petrobactin
Names
	Preferred IUPAC name 4-[4-[3-[(3,4-dihydroxybenzoyl)amino]propylamino]butylamino]-2-[2-[4-[3-[(3,4-dihydroxybenzoyl)amino]propylamino]butylamino]-2-oxoethyl]-2-hydroxy-4-oxobutanoic acid
Identifiers
CAS Number	545434-89-7 [];
3D model (JSmol)	Interactive image; H+: Interactive image;
ChEBI	H+: CHEBI:142778;
ChemSpider	9586399;
KEGG	C22273;
PubChem CID	11411510;
	InChI InChI=1S/C34H50N6O11/c41-25-9-7-23(19-27(25)43)31(47)39-17-5-13-35-11-1-3-15-37-29(45)21-34(51,33(49)50)22-30(46)38-16-4-2-12-36-14-6-18-40-32(48)24-8-10-26(42)28(44)20-24/h7-10,19-20,35-36,41-44,51H,1-6,11-18,21-22H2,(H,37,45)(H,38,46)(H,39,47)(H,40,48)(H,49,50) Key: GKIMOVAPSAVJHZ-UHFFFAOYSA-N; H+: InChI=1S/C34H50N6O11/c41-25-9-7-23(19-27(25)43)31(47)39-15-3-1-11-35-13-5-17-37-29(45)21-34(51,33(49)50)22-30(46)38-18-6-14-36-12-2-4-16-40-32(48)24-8-10-26(42)28(44)20-24/h7-10,19-20,35-36,41-44,51H,1-6,11-18,21-22H2,(H,37,45)(H,38,46)(H,39,47)(H,40,48)(H,49,50)/p+1 Key: SESZZOOISCLDTE-UHFFFAOYSA-O;
	SMILES C1=CC(=C(C=C1C(=O)NCCCNCCCCNC(=O)CC(CC(=O)NCCCCNCCCNC(=O)C2=CC(=C(C=C2)O)O)(C(=O)O)O)O)O; H+: C(=O)([O-])C(CC(=O)NCCC[NH2+]CCCCNC(C1=CC=C(C(=C1)O)O)=O)(CC(=O)NCCC[NH2+]CCCCNC(C2=CC=C(C(=C2)O)O)=O)O;
Properties
Chemical formula	C34H50N6O11
Molar mass	718.79 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

Petrobactin is a bis-catechol siderophore found in M. hydrocarbonoclasticus, A. macleodii, and the anthrax-producing B. anthracis.^[2] Like other siderophores petrobactin is a highly specific iron(III) transport ligand, contributing to the marine microbial uptake of environmental iron.^[2]^[3]

The iron-chelated petrobactin complex readily undergoes a photolytic oxidative decarboxylation due to its α-hydroxy carboxylate group, converting iron(III) to the more biologically useful iron(II).^[4]

3D structure of petrobactin-iron complex generated with OPLS-AA forcefield in MOE.

[1]

[2]

[3]

[4]

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Category

Petrobactin

Biosynthesis

References

Related Articles

Related Articles

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