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Key Documents

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Takuya Iwama et al.
Cancer cell international, 21(1), 21-21 (2021-01-08)
Colorectal cancers develop through several pathways, including the adenoma-carcinoma sequence and colitis-associated carcinogenesis. An altered intestinal microflora has been reported to be associated with the development and progression of colorectal cancer via these pathways. We identified Lactobacillus casei-derived ferrichrome as
Microbial iron compounds.
J B Neilands
Annual review of biochemistry, 50, 715-731 (1981-01-01)
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].
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