Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge

Sayo Ito; Yumiko Sasaki; Yasuyuki Takahashi; Shigeru Ohba; Yuzo Nishida

doi:10.1515/znc-1999-7-815

Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge

Sayo Ito, Yumiko Sasaki, Yasuyuki Takahashi, Shigeru Ohba, Yuzo Nishida

Department of Humanities and Social Sciences

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The (μ-oxo)(μ-carbonato)diiron(III) complex with H₂(tfda) (H₂(tfda) = 2-aminomethyl-tetrahydrofuran-N,N-diacetic acid) exhibited high activity for hydroxylation of 2'-deoxyguanosine in the presence of hydrogen peroxide, giving 8-hydroxydeoxyguanosine, but its hydroxylation activity towards other nucleosides such as 2'-deoxyadenosine, adenosine or thymidine was found negligible. In the case of the Fe(III)-(eda) complex (H₂(eda) = 2-methoxyethylamine-N,N-diacetic acid), hydroxylation occurred mainly at the sugar site, converting 2'-deoxyguanosine to guanosine. Based on the spectroscopic and structural properties of these iron(III) compounds, it seems most likely that an intrinsic active species for hydroxylation should be an electrophilic peroxide adduct of the (μ-oxo)diiron(III) core with η¹-coordination mode, while the contribution of OH· to the hydroxylation reaction of nucleosides is ruled out.

Original language	English
Pages (from-to)	554-561
Number of pages	8
Journal	Zeitschrift fur Naturforschung - Section C Journal of Biosciences
Volume	54
Issue number	7-8
DOIs	https://doi.org/10.1515/znc-1999-7-815
Publication status	Published - 1999

Keywords

8-Hydroxydeoxyguanosine
Iron(III)-peroxide Adduct
Nucleosides
Oxygenation

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)

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title = "Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge",

abstract = "The (μ-oxo)(μ-carbonato)diiron(III) complex with H2(tfda) (H2(tfda) = 2-aminomethyl-tetrahydrofuran-N,N-diacetic acid) exhibited high activity for hydroxylation of 2'-deoxyguanosine in the presence of hydrogen peroxide, giving 8-hydroxydeoxyguanosine, but its hydroxylation activity towards other nucleosides such as 2'-deoxyadenosine, adenosine or thymidine was found negligible. In the case of the Fe(III)-(eda) complex (H2(eda) = 2-methoxyethylamine-N,N-diacetic acid), hydroxylation occurred mainly at the sugar site, converting 2'-deoxyguanosine to guanosine. Based on the spectroscopic and structural properties of these iron(III) compounds, it seems most likely that an intrinsic active species for hydroxylation should be an electrophilic peroxide adduct of the (μ-oxo)diiron(III) core with η1-coordination mode, while the contribution of OH· to the hydroxylation reaction of nucleosides is ruled out.",

keywords = "8-Hydroxydeoxyguanosine, Iron(III)-peroxide Adduct, Nucleosides, Oxygenation",

author = "Sayo Ito and Yumiko Sasaki and Yasuyuki Takahashi and Shigeru Ohba and Yuzo Nishida",

year = "1999",

doi = "10.1515/znc-1999-7-815",

language = "English",

volume = "54",

pages = "554--561",

journal = "Zeitschrift fur Naturforschung. Section C: Biosciences",

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TY - JOUR

T1 - Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge

AU - Ito, Sayo

AU - Sasaki, Yumiko

AU - Takahashi, Yasuyuki

AU - Ohba, Shigeru

AU - Nishida, Yuzo

PY - 1999

Y1 - 1999

N2 - The (μ-oxo)(μ-carbonato)diiron(III) complex with H2(tfda) (H2(tfda) = 2-aminomethyl-tetrahydrofuran-N,N-diacetic acid) exhibited high activity for hydroxylation of 2'-deoxyguanosine in the presence of hydrogen peroxide, giving 8-hydroxydeoxyguanosine, but its hydroxylation activity towards other nucleosides such as 2'-deoxyadenosine, adenosine or thymidine was found negligible. In the case of the Fe(III)-(eda) complex (H2(eda) = 2-methoxyethylamine-N,N-diacetic acid), hydroxylation occurred mainly at the sugar site, converting 2'-deoxyguanosine to guanosine. Based on the spectroscopic and structural properties of these iron(III) compounds, it seems most likely that an intrinsic active species for hydroxylation should be an electrophilic peroxide adduct of the (μ-oxo)diiron(III) core with η1-coordination mode, while the contribution of OH· to the hydroxylation reaction of nucleosides is ruled out.

AB - The (μ-oxo)(μ-carbonato)diiron(III) complex with H2(tfda) (H2(tfda) = 2-aminomethyl-tetrahydrofuran-N,N-diacetic acid) exhibited high activity for hydroxylation of 2'-deoxyguanosine in the presence of hydrogen peroxide, giving 8-hydroxydeoxyguanosine, but its hydroxylation activity towards other nucleosides such as 2'-deoxyadenosine, adenosine or thymidine was found negligible. In the case of the Fe(III)-(eda) complex (H2(eda) = 2-methoxyethylamine-N,N-diacetic acid), hydroxylation occurred mainly at the sugar site, converting 2'-deoxyguanosine to guanosine. Based on the spectroscopic and structural properties of these iron(III) compounds, it seems most likely that an intrinsic active species for hydroxylation should be an electrophilic peroxide adduct of the (μ-oxo)diiron(III) core with η1-coordination mode, while the contribution of OH· to the hydroxylation reaction of nucleosides is ruled out.

KW - 8-Hydroxydeoxyguanosine

KW - Iron(III)-peroxide Adduct

KW - Nucleosides

KW - Oxygenation

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ER -

Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge

Abstract

Keywords

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