A Water-Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase-Like Catalytic Activities

被引：130

作者：

Kumakura, Fumio ^{[1
]}

Mishra, Beena ^{[2
]}

Priyadarsini, K. Indira ^{[2
]}

Iwaoka, Michio ^{[1
]}

机构：

[1] Tokai Univ, Sch Sci, Dept Chem, Hiratsuka, Kanagawa 2591292, Japan

[2] Bhabha Atom Res Ctr, Radiat & Photochem Div, Bombay 400085, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 03期

关键词：

Antioxidants; Enzyme models; Peroxides; Protein folding; Selenium; RIBONUCLEASE-A; SELENOMETHIONINE; REGENERATION; DERIVATIVES; OXIDATION; ENERGIES; REAGENT;

D O I：

10.1002/ejoc.200901114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Antioxidative catalytic activities of trans-3,4-dihydroxyselenolane (DHSred), a water-soluble cyclic selenide, were investigated in the reaction of hydrogen peroxide with three different thiol substrates, monothiol glutathione (GSH), dithiol dithiothreitol (DTTred), and polythiol reduced ribonuclease A (RNase A) having eight thiol groups along the polypeptide chain For all the thiol substrates, DHSred exhibited higher glutathione peroxidase (GPx)-like antioxidative catalytic activities than the corresponding linear selenide, that is, Se(CH2CH2OH)(2) The rate-determining step of the catalytic cycle was unambiguously assigned to the oxidation process of the selenide rather than the reduction process of the selenoxide intermediate The enhanced catalytic activities of DHSred can be ascribed to the cyclic structure, which elevates the HOMO energy level and makes the selenium atom more exposed to the surroundings.

引用

页码：440 / 445

页数：6

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