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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U2 - 10.1515/znc-1999-7-815
DO - 10.1515/znc-1999-7-815
M3 - Article
AN - SCOPUS:0032831676
VL - 54
SP - 554
EP - 561
JO - Zeitschrift fur Naturforschung. Section C: Biosciences
JF - Zeitschrift fur Naturforschung. Section C: Biosciences
SN - 0939-5075
IS - 7-8
ER -