Reactions between iron(III) and catechol (o-dihydroxybenzene). Part II. Equilibria and kinetics of the redox reaction in aqueous acid solution

Mentasti, Edoar̈do; Pelizzetti, Ezio; Saini, G.

doi:10.1039/dt9730002609

Cited by 72 publications

(52 citation statements)

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“…3 and 4. The mechanism of the shape control by odihydroxybenzene (catechol) seems to be the same as with hydroquinone, since it can also take the quinone form by the redox reaction with Fe 3ϩ (23) and transform to humic compounds via oxidative polymerization (24).…”

Section: Mechanism Of Shape Control By Hqmentioning

confidence: 99%

Shape Control of Monodisperse Hematite Particles by Organic Additives in the Gel–Sol System

Sugimoto

Itoh

Mochida

1998

Journal of Colloid and Interface Science

110

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Section: Mechanism Of Shape Control By Hqmentioning

confidence: 99%

Shape Control of Monodisperse Hematite Particles by Organic Additives in the Gel–Sol System

Sugimoto

Itoh

Mochida

1998

Journal of Colloid and Interface Science

110

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“…The methanol extracts were concentrated to a paste by rotary evaporation in acid-cleaned flasks and resuspended in a small volume (1-5 ml) of buffer: catechol-containing extracts were dissolved in 0.01 M phosphate buffer at pH 7 to minimize irreversible oxidation of the catechol functionality at low pH (Mentasti et al 1973), while extracts that were not catechol reactive were resuspended in 0.01 M acetate buffer at pH 4. Partial purification of the siderophores was achieved by fractionation of the extracts on a Sephadex LH-20 (Pharmacia) column (50 by 1 cm) in their respective buffers.…”

Section: Methodsmentioning

confidence: 99%

The importance of siderophores in iron nutrition of heterotrophic marine bacteria

Granger

Price

1999

Limnology & Oceanography

179

162

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Recent studies demonstrate that dissolved iron in seawater is bound to strong organic complexes that have stability constants comparable to those of microbial iron chelates. We examined iron acquisition by seven strains of heterotrophic marine bacteria from a number of siderophore-iron complexes, including desferrioxamine B (DFB) and marine siderophores partially purified from iron-limited cultures. Hydroxamate siderophores were detected in the supernatants of four strains, one of which also produced a catechol. All strains transported iron bound to siderophores regardless of whether or not they produced their own, and the majority took up iron bound to DFB. Uptake rates of Fe siderophores were similar among iron-limited strains and among ligands. Transport of FeDFB by strain Neptune was enhanced 20 times by iron limitation, whereas uptake of unchelated iron (FeЈ) did not saturate at the highest concentration tested and was not regulated by the iron nutritional status of the cells. The half-saturation constant for uptake of FeDFB by Neptune was 15 nM, the lowest reported for an Fe siderophore in any microorganism. Iron uptake by the catechol-producing strain, LMG1, differed markedly in two respects from the other strains: LMG1 could not take up iron bound to DFB; furthermore, transport of FeЈ by iron-limited LMG1 was 10 times faster than the other strains and was upregulated 46 times compared to Fe-sufficient cells. Experimental evidence suggests that iron transport by LMG1 may be mediated by surface-associated catechol siderophores that scavenge inorganic ferric species as well as iron bound to weaker complexes, such as EDTA (ethylenediaminetetraacetic acid). The combined results of the study highlight the importance of siderophores in iron transport by heterotrophic marine bacteria and suggest, by inference, that bacteria may rely on siderophores to acquire iron in situ.

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“…Oxidation of catechol, Dopa, and several other 3,4-dihydroxy catechols by Fe(III) occurs in aqueous acidic solution (0.01-1M H + ) forming quinone and two equivalents of Fe(II) [80][81][82]. A semiquinone radical intermediate is formed during the rate-determining step, which is subsequently oxidized to quinone by a second equivalent of Fe(III) [81] (Fig.…”

Section: Oxidation Of Catechols By Fe(iii) In Mussel Plaquesmentioning

confidence: 99%

“…A semiquinone radical intermediate is formed during the rate-determining step, which is subsequently oxidized to quinone by a second equivalent of Fe(III) [81] (Fig. 11).…”

Section: Oxidation Of Catechols By Fe(iii) In Mussel Plaquesmentioning

confidence: 99%

Siderophores and mussel foot proteins: the role of catechol, cations, and metal coordination in surface adhesion

Maier

Butler

2017

J Biol Inorg Chem

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Metal coordination, hydrogen bonding, redox reactions, and covalent crosslinking are seemingly disparate chemical and physicochemical processes that are all accomplished in natural materials by the catechol functional group. This review focuses on the reactivity of catechols in tris-2,3-dihydroxybenzoyl-containing microbial siderophores and synthetic analogs, as well as Dopa-(3,4-dihydroxyphenylalanine)-containing mussel foot proteins that adhere to surfaces in aqueous conditions.Mussel foot proteins with a high content of Dopa and cationic amino acids, Lys and Arg, adhere strongly to mica, an aluminosilicate mineral, in aqueous conditions. The siderophore cyclic trichrysobactin, tris-(2,3-dihydroxybenzoyl-D-Lys-L-Ser) and related synthetic analogs in which the tri-Ser macrolactone is replaced by Tren, tris-(2-aminoethyl)amine, also adheres strongly to mica. Variation in the nature of the catechol and cationic groups in synthetic analogs reveals a synergism between the cationic amino acid and the catechol, required for strong aqueous adhesion. Autoxidation and iron(III)-catalyzed oxidation of 2,3-dihydroxy and 3,4-dihydroxy catechols is also considered. These siderophore analogs provide a platform to understand catechol interactions and reactivity on surfaces, which may ultimately improve the design of synthetic materials that address diverse challenges in medicine, materials science, as well as other disciplines, in which surface adhesion in aqueous conditions is important.

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Reactions between iron(III) and catechol (o-dihydroxybenzene). Part II. Equilibria and kinetics of the redox reaction in aqueous acid solution

Cited by 72 publications

References 0 publications

Shape Control of Monodisperse Hematite Particles by Organic Additives in the Gel–Sol System

Shape Control of Monodisperse Hematite Particles by Organic Additives in the Gel–Sol System

The importance of siderophores in iron nutrition of heterotrophic marine bacteria

Siderophores and mussel foot proteins: the role of catechol, cations, and metal coordination in surface adhesion

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