Ferrichrome

Not to be confused with ferrochrome.
For the audio tape formulation, see Compact Cassette tape types and formulations § Ferrichrome.
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)
ChemSpider
ECHA InfoCard 100.036.081 Edit this at Wikidata
EC Number
  • 239-706-0
UNII
  • InChI=1S/C27H42N9O12.Fe/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39;/h19-21H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44);/q-3;+3
    Key: GGUNGDGGXMHBMJ-UHFFFAOYSA-N
  • 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 740.529 g·mol−1
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, and has been found to be produced by fungi of the genera Aspergillus, Ustilago, and Penicillium.[1] However, at the time there was no understanding regarding its involvement and contribution to iron transport.[2] It was not until 1957 because of Joe Neilands' work, where he first noted that Ferrichrome was able to act as an iron transport agent.

  1. ^ Ferrichrome Archived 2010-01-13 at the Wayback Machine, Virtual Museum of Minerals and Molecules, University of Wisconsin
  2. ^ Kenneth Raymond - The Human/Bacterial Arms Race for Iron, retrieved 2021-12-04