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F8014

Sigma-Aldrich

Ferrichrome Iron-free from Ustilago sphaerogena

Synonym(s):

Deferriferrichrome

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About This Item

Empirical Formula (Hill Notation):
C27H45N9O12
CAS Number:
34787-28-5
Molecular Weight:
687.70
UNSPSC Code:
12352005
PubChem Substance ID:
24894955
NACRES:
NA.25

storage temp.

2-8°C

Quality Level

200

SMILES string

C\C(CC(O)=O)=C/C1=[O][Fe]2345ON1CCCC6NC(=O)CNC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCCN(O2)C(\C=C(\C)CC(O)=O)=[O]3)NC(=O)C(CCCN(O4)C(\C=C(/C)CC(O)=O)=[O]5)NC6=O

InChI

1S/C27H45N9O12/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/h19-21,46-48H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44)/t19-,20-,21-/m0/s1

InChI key

ZFDAUYPBCXMSBF-ACRUOGEOSA-N

Biochem/physiol Actions

Growth-promoting iron chelator

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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K L Constantine et al.
Biopolymers, 30(3-4), 239-256 (1990-01-01)
We have applied computational procedures that utilize nmr data to model the solution conformation of ferrichrome, a rigid microbial iron transport cyclohexapeptide of known x-ray crystallographic structure [D. van der Helm et al. (1980) J. Am. Chem. Soc. 102, 4224-4231].
Sijing Wang et al.
Applied and environmental microbiology, 86(7) (2020-02-02)
The siderophore synthetic system in Shewanella species is able to synthesize dozens of macrocyclic siderophores in vitro with synthetic precursors. In vivo, however, although three siderophores are produced naturally in Shewanella algae B516, which carries a lysine decarboxylase (AvbA) specific
Guozhang Zou et al.
Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 18(1), 63-74 (2005-05-04)
Desferriferricrocin is a cyclic hexa-peptide siderophore with three hydroxamates as primary coordination groups. It forms metal complexes with Fe(III), Cr(III), Al(III), Ga(III), Cu(II), and Zn(II). These complexes were prepared and characterized using UV-vis, circular dichroism spectroscopy (CD), nuclear magnetic resonance
J D Herscheid et al.
Nuclear medicine communications, 7(1), 53-57 (1986-01-01)
The biodistribution of 67Ga-labelled complexes of some mono- and di-N-hydroxyamino acid derivatives and of two siderophores (trihydroxamates) were evaluated in Rhabdomyosarcoma-bearing rats. It was found that the mono- and dihydroxamates could not enhance the tumour-localizing properties of 67Ga-citrate, while the
Microbial iron compounds.
J B Neilands
Annual review of biochemistry, 50, 715-731 (1981-01-01)
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