Ferrie stability constants of representative marine siderophores

Marinobactins, aquachelins, and petrobactin

Guangping Zhang, Shady Amin, Frithjof C. Küpper, Pamela D. Holt, Carl J. Carrano, Allson Butler

    Research output: Contribution to journalArticle

    Abstract

    The coordination of iron(III) to the marine amphiphilic marinobactin and aquachelin siderophores, as well as to petrobactin, an unusual 3,4-dihydroxybenzoyl siderophore is reported. Potentiometric titrations were performed on the apo siderophore to determine the ligand pK a values, as well as the complex formed with addition of 1 equiv of Fe(III). The log K ML values for Fe(III)-marinobactin-E and Fe(III)-aquachelin-C are 31.80 and 31.4, respectively, consistent with the similar coordination environment in each complex, while log K ML for Fe(lll)-petrobactin is estimated to be about 43. The pK a of the β-hydroxyaspartyl hydroxyl group was determined to be 10.8 by 1H NMR titration. 13C NMR and IR spectroscopy were used to investigate Ga(III) coordination to the marinobactins. The coordination-induced shifts (CIS) in the 13C NMR spectrum of Ga(III)-marinobactin-C compared to apo-marinobactin-C indicates that the hydroxamate groups are coordinated to Ga(III); however, the lack of CISs for the carbons of the β-hydroxyamide group suggests this moiety is not coordinated in the Ga(III) complex. Differences in the IR spectrum of Ga(lll)-marinobactin-C and Fe(III)-marinobactin-C in the 1600-1700 cm -1 region also corroborates Fe(III) is coordinated to the β-hydroxyamide moiety, whereas Ga(III) is not coordinated.

    Original languageEnglish (US)
    Pages (from-to)11466-11473
    Number of pages8
    JournalInorganic Chemistry
    Volume48
    Issue number23
    DOIs
    StatePublished - Dec 1 2009

    Fingerprint

    Siderophores
    Titration
    Nuclear magnetic resonance
    titration
    nuclear magnetic resonance
    Hydroxyl Radical
    Commonwealth of Independent States
    Nuclear magnetic resonance spectroscopy
    Infrared spectroscopy
    Carbon
    Iron
    Ligands
    iron
    ligands
    petrobactin
    carbon
    shift
    spectroscopy

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Inorganic Chemistry

    Cite this

    Zhang, G., Amin, S., Küpper, F. C., Holt, P. D., Carrano, C. J., & Butler, A. (2009). Ferrie stability constants of representative marine siderophores: Marinobactins, aquachelins, and petrobactin. Inorganic Chemistry, 48(23), 11466-11473. https://doi.org/10.1021/ic901739m

    Ferrie stability constants of representative marine siderophores : Marinobactins, aquachelins, and petrobactin. / Zhang, Guangping; Amin, Shady; Küpper, Frithjof C.; Holt, Pamela D.; Carrano, Carl J.; Butler, Allson.

    In: Inorganic Chemistry, Vol. 48, No. 23, 01.12.2009, p. 11466-11473.

    Research output: Contribution to journalArticle

    Zhang, G, Amin, S, Küpper, FC, Holt, PD, Carrano, CJ & Butler, A 2009, 'Ferrie stability constants of representative marine siderophores: Marinobactins, aquachelins, and petrobactin', Inorganic Chemistry, vol. 48, no. 23, pp. 11466-11473. https://doi.org/10.1021/ic901739m
    Zhang, Guangping ; Amin, Shady ; Küpper, Frithjof C. ; Holt, Pamela D. ; Carrano, Carl J. ; Butler, Allson. / Ferrie stability constants of representative marine siderophores : Marinobactins, aquachelins, and petrobactin. In: Inorganic Chemistry. 2009 ; Vol. 48, No. 23. pp. 11466-11473.
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    abstract = "The coordination of iron(III) to the marine amphiphilic marinobactin and aquachelin siderophores, as well as to petrobactin, an unusual 3,4-dihydroxybenzoyl siderophore is reported. Potentiometric titrations were performed on the apo siderophore to determine the ligand pK a values, as well as the complex formed with addition of 1 equiv of Fe(III). The log K ML values for Fe(III)-marinobactin-E and Fe(III)-aquachelin-C are 31.80 and 31.4, respectively, consistent with the similar coordination environment in each complex, while log K ML for Fe(lll)-petrobactin is estimated to be about 43. The pK a of the β-hydroxyaspartyl hydroxyl group was determined to be 10.8 by 1H NMR titration. 13C NMR and IR spectroscopy were used to investigate Ga(III) coordination to the marinobactins. The coordination-induced shifts (CIS) in the 13C NMR spectrum of Ga(III)-marinobactin-C compared to apo-marinobactin-C indicates that the hydroxamate groups are coordinated to Ga(III); however, the lack of CISs for the carbons of the β-hydroxyamide group suggests this moiety is not coordinated in the Ga(III) complex. Differences in the IR spectrum of Ga(lll)-marinobactin-C and Fe(III)-marinobactin-C in the 1600-1700 cm -1 region also corroborates Fe(III) is coordinated to the β-hydroxyamide moiety, whereas Ga(III) is not coordinated.",
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    AU - Zhang, Guangping

    AU - Amin, Shady

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    AU - Holt, Pamela D.

    AU - Carrano, Carl J.

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    AB - The coordination of iron(III) to the marine amphiphilic marinobactin and aquachelin siderophores, as well as to petrobactin, an unusual 3,4-dihydroxybenzoyl siderophore is reported. Potentiometric titrations were performed on the apo siderophore to determine the ligand pK a values, as well as the complex formed with addition of 1 equiv of Fe(III). The log K ML values for Fe(III)-marinobactin-E and Fe(III)-aquachelin-C are 31.80 and 31.4, respectively, consistent with the similar coordination environment in each complex, while log K ML for Fe(lll)-petrobactin is estimated to be about 43. The pK a of the β-hydroxyaspartyl hydroxyl group was determined to be 10.8 by 1H NMR titration. 13C NMR and IR spectroscopy were used to investigate Ga(III) coordination to the marinobactins. The coordination-induced shifts (CIS) in the 13C NMR spectrum of Ga(III)-marinobactin-C compared to apo-marinobactin-C indicates that the hydroxamate groups are coordinated to Ga(III); however, the lack of CISs for the carbons of the β-hydroxyamide group suggests this moiety is not coordinated in the Ga(III) complex. Differences in the IR spectrum of Ga(lll)-marinobactin-C and Fe(III)-marinobactin-C in the 1600-1700 cm -1 region also corroborates Fe(III) is coordinated to the β-hydroxyamide moiety, whereas Ga(III) is not coordinated.

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