20008-20-2

Basic information

• Product Name: FERRIOXAMINE E
• Synonyms: 1,12,23-Trihydroxy-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexoneIron(III)complex;Ferrioxamine;Ferrioxamine E from Streptomyces antibioticus
• CAS NO: 20008-20-2
• Molecular Formula: C27H45FeN6O9
• Molecular Weight: 653.526
• Mol File: 20008-20-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: FERRIOXAMINE E(CAS DataBase Reference)
• NIST Chemistry Reference: FERRIOXAMINE E(20008-20-2)
• EPA Substance Registry System: FERRIOXAMINE E(20008-20-2)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 20008-20-2(Hazardous Substances Data)

Usage

Description

Ferrioxamine E is a bacterial siderophore produced by a variety of bacteria including S. glaucescens, M. luteus, and P. mendocina. Ferrioxamines, including ferrioxamine E, are the sole iron source for Salmonella, and have been used as growth enriching agents in the detection of Salmonella in food and industrial applications.

InChI:InChI=1/C27H45N6O9.Fe/c34-22-10-14-26(38)32(41)20-8-3-6-18-30-24(36)12-15-27(39)33(42)21-9-2-5-17-29-23(35)11-13-25(37)31(40)19-7-1-4-16-28-22;/h1-21H2,(H,28,34)(H,29,35)(H,30,36);/q-3;+3

Relevant articles and documents

Forward and reverse (Retro) Iron(III) or gallium(III) desferrioxamine e and ring-expanded analogues prepared using metal-templated synthesis from endo -hydroxamic acid monomers

A metal-templated synthesis (MTS) approach was used to preorganize the forward endo-hydroxamic acid monomer 4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoic acid (for-PBH) about iron(III) in a 1:3 metal/ligand ratio to furnish the iron(III) siderophore for-[Fe(DFOE)] (ferrioxamine E) following peptide coupling. Substitution of for-PBH with the reverse (retro) hydroxamic acid analogue 3-(6-amino-N-hydroxyhexanamido)propanoic acid (ret-PBH) furnished ret-[Fe(DFOE)] (ret-ferrioxamine E). As isomers, for-[Fe(DFOE)] and ret-[Fe(DFOE)] gave identical mass spectrometry signals ([M + H+]+, m/zcalc 654.3, m/zobs 654.3), yet for-[Fe(DFOE)] eluted in a more polar window (tR = 23.44 min) than ret-[Fe(DFOE)] (tR = 28.13 min) on a C18 reverse-phase high-performance liquid chromatography (RP-HPLC) column. for-[Ga(DFOE)] (tR = 22.99 min) and ret-[Ga(DFOE)] (tR = 28.11 min) were prepared using gallium(III) as the metal-ion template and showed the same trend for the retention time. Ring-expanded analogues of for-[Fe(DFOE)] and ret-[Fe(DFOE)] were prepared from endo-hydroxamic acid monomers with one additional methylene unit in the amine-containing region, 4-[(6-aminohexyl)(hydroxy)amino]-4-oxobutanoic acid (for-HBH) or 3-(7-amino-N-hydroxyheptanamido)propanoic acid (ret-HBH), to give the corresponding tris(homoferrioxamine E) macrocycles, for-[Fe(HHDFOE)] or ret-[Fe(HHDFOE)] ([M + H+]+, m/zcalc 696.3, m/zobs 696.4). The MTS reaction using a constitutional isomer of for-HBH that transposed the methylene unit to the carboxylic acid containing region, 5-[(5-aminopentyl)(hydroxy)amino]-5-oxopentanoic acid (for-PPH), gave the macrocycle for-[Fe(HPDFOE)] in a yield significantly less than that for for-[Fe(HHDFOE)], with the gallium(III) analogue for-[Ga(HPDFOE)] unable to be detected. The work demonstrates the utility and limits of MTS for the assembly of macrocyclic siderophores from endo-hydroxamic acid monomers. Indirect measures (RP-HPLC order of elution, c log P values, molecular mechanics, and density functional theory calculations) of the relative water solubility of the ligands, the iron(III) macrocycles, and the apomacrocycles were consistent in identifying for-DFOE as the most water-soluble macrocycle from for-DFOE, ret-DFOE, for-HHDFOE, ret-HHDFOE, and for-HPDFOE. From this group, only for-DFOE is known in nature, which could suggest that water solubility is an important trait in its natural selection.