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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)554-561
Number of pages8
JournalZeitschrift fur Naturforschung - Section C Journal of Biosciences
Volume54
Issue number7-8
Publication statusPublished - 1999 Jul

Fingerprint

Hydroxylation
Oxygenation
nucleosides
Peroxides
hydroxylation
peroxides
Nucleosides
Iron
iron
Deoxyguanosine
Iron Compounds
Iron compounds
guanosine
Acids
Guanosine
acids
adenosine
thymidine
Sugars
Adenosine

Keywords

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

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge. / Ito, Sayo; Sasaki, Yumiko; Takahashi, Yasuyuki; Ohba, Shigeru; Nishida, Yuzo.

In: Zeitschrift fur Naturforschung - Section C Journal of Biosciences, Vol. 54, No. 7-8, 07.1999, p. 554-561.

Research output: Contribution to journalArticle

Ito, Sayo ; Sasaki, Yumiko ; Takahashi, Yasuyuki ; Ohba, Shigeru ; Nishida, Yuzo. / Oxygenation of nucleosides by peroxide adduct of binuclear iron(III) complex with a μ-oxo bridge. In: Zeitschrift fur Naturforschung - Section C Journal of Biosciences. 1999 ; Vol. 54, No. 7-8. pp. 554-561.
@article{0112ce2d70594bb1a00ccb9a6c0d1b9c,
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",
month = "7",
language = "English",
volume = "54",
pages = "554--561",
journal = "Zeitschrift fur Naturforschung - Section C Journal of Biosciences",
issn = "0939-5075",
publisher = "Verlag der Zeitschrift fur Naturforschung",
number = "7-8",

}

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 - 1999/7

Y1 - 1999/7

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

UR - http://www.scopus.com/inward/record.url?scp=0032831676&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032831676&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0032831676

VL - 54

SP - 554

EP - 561

JO - Zeitschrift fur Naturforschung - Section C Journal of Biosciences

JF - Zeitschrift fur Naturforschung - Section C Journal of Biosciences

SN - 0939-5075

IS - 7-8

ER -