Formation of a spirodiazaselenurane and its corresponding azaselenonium derivatives from the oxidation of 2,2′-selenobis(benzamide). Structure, properties and glutathione peroxidase activity
作者:Dušan Kuzma、Masood Parvez、Thomas George Back
DOI:10.1039/b710685h
日期:——
The oxidation of 2,2â²-selenobis(benzamide) with N-chlorosuccinimide or hydrogen peroxide afforded the corresponding stable azaselenonium chloride and hydroxide, respectively. Both structures were characterized by spectroscopic and X-ray crystallographic methods. Each contains a covalent NâSe bond, as well as a noncovalent interaction between the selenium atom and the carbonyl oxygen atom of the other amide moiety. The treatment of the azaselenonium chloride with an excess of potassium hydride in DMSO-d6 afforded the corresponding spirodiazaselenurane species, which proved hydrolytically unstable, but was characterized by NMR spectroscopy. The azaselenonium chloride displayed significant glutathione peroxidase-like catalytic activity in an assay with benzyl thiol and either hydrogen peroxide or tert-butyl hydroperoxide.
用N-氯代琥珀酰亚胺或过氧化氢氧化2,2-硒二(苯甲酰胺),分别得到相应的稳定的氯化氮杂硒铵和氢氧化氮杂硒铵。两种结构均通过光谱和X射线晶体学方法进行了表征。每个都包含一个共价 N-Se 键,以及硒原子和另一个酰胺部分的羰基氧原子之间的非共价相互作用。用过量的氢化钾在 DMSO-d6 中处理氯化氮杂硒铵,得到相应的螺二氮杂硒脲烷物种,其被证明水解不稳定,但通过 NMR 光谱进行了表征。在使用苄硫醇和过氧化氢或叔丁基氢过氧化物进行的测定中,氮杂硒铵氯化物显示出显着的谷胱甘肽过氧化物酶样催化活性。