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Ferrichrome

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Ferrichrome

Ferrichrome (sticks) bound to an iron atom (orange)
Names
IUPAC name
N-[3-[4,16-bis[3-[acetyl(oxido)amino]propyl]-2,5,8,11,14,17-hexaoxo-3,6,9,12,15,18-hexazacyclooctadec-1-yl]propyl]-N-oxidoacetamide; iron(3+)
Identifiers
3D model (JSmol)
ECHA InfoCard 100.036.081 Edit this at Wikidata
  • CC(=O)N(CCCC1C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NCC(=O)N1)CCCN(C(=O)C)[O-])CCCN(C(=O)C)[O-])[O-].[Fe+3]
Properties
C27H42FeN9O12
Molar mass 740.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ferrichrome is a cyclic hexa-peptide that forms a complex with iron atoms. It is a siderophore composed of three glycine and three modified ornithine residues with hydroxamate groups [-N(OH)C(=O)C-]. The 6 oxygen atoms from the three hydroxamate groups bind Fe(III) in near perfect octahedral coordination.

Ferrichrome was first isolated in 1952, has been found to be produced by fungi of the genera Aspergillus, Ustilago, and Penicillium.[1]

References

  1. ^ Ferrichrome, Virtual Museum of Minerals and Molecules, University of Wisconsin