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Thiol-targeted introduction of selenocysteine to polypeptides for synthesis of glutathione peroxidase mimics.

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タイトル: Thiol-targeted introduction of selenocysteine to polypeptides for synthesis of glutathione peroxidase mimics.
著者: Haratake, Mamoru / Sakano, Tsunanori / Fuchigami, Takeshi / Nakayama, Morio
発行日: 2011年 7月 1日
出版者: The Royal Society of Chemistry
引用: Metallomics, 3(7), pp.702-709; 2011
抄録: Because the seleno-l-cysteine (SeCys or Sec) insertion into selenoproteins occurs by a specific translational control process, it is quite difficult to express the SeCys-containing polypeptides even by the state-of-the-art genetic engineering techniques. In this paper, we describe a convenient synthetic method for the selective introduction of a SeCys derivative to polypeptides under physiological conditions. One SeCys residue in the seleno-l-cystine (SeCys-Se-Se-SeCys) methyl ester was first substituted with the Boc-protected penicillamine (Pen) methyl ester to form selenenylsulfide (SeCys-Se-S-Pen), an intermediate in the cellular glutathione peroxidase (GPx) catalytic cycle. Subsequently, the SeCys-Pen was coupled with the thiol-specific N-carboxymethylmaleimide through the α-amino group of the SeCys {[2-(N-maleimidyl)-1-oxo-ethyl-SeCys-methyl-Se-yl]-S-Pen methyl ester, MOE-SeCys-Pen}. The use of the MOE-SeCys-Pen allowed the selective introduction of the SeCys moiety to human serum albumin by alkylation of the thiol at its cysteine34, which generated the GPx-like activity responsible for the selenium atom in the MOE-SeCys-Pen. Consequently, this synthetic method will allow generating SeCys-containing artificial polypeptides with a GPx-like activity.
URI: http://hdl.handle.net/10069/27420
ISSN: 17565901
DOI: 10.1039/c1mt00001b
PubMed ID: 21365111
権利: © 2011 The Royal Society of Chemistry.
資料タイプ: Journal Article
原稿種類: author
出現コレクション:050 学術雑誌論文

引用URI : http://hdl.handle.net/10069/27420



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