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Title
Japanese: 
English:Modeling the Catalytic Cycle of Glutathione Peroxidase by Nuclear Magnetic Resonance Spectroscopic Analysis of Selenocysteine Selenenic Acids 
Author
Japanese: 増田涼介, 木村龍太郎, 唐﨑貴史, 佐瀬祥平, 後藤 敬.  
English: Ryosuke Masuda, Ryutaro Kimura, Takafumi Karasaki, Shohei Sase, Kei Goto.  
Language English 
Journal/Book name
Japanese: 
English:Journal of the American Chemical Society 
Volume, Number, Page Vol. 143    issue 17    pp. 6345–6350
Published date Apr. 22, 2021 
Publisher
Japanese: 
English:American Chemical Society 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
File
Official URL https://pubs.acs.org/doi/full/10.1021/jacs.1c02383
 
DOI https://doi.org/10.1021/jacs.1c02383
Abstract Although selenocysteine selenenic acids (Sec–SeOHs) have been recognized as key intermediates in the catalytic cycle of glutathione peroxidase (GPx), examples of the direct observation of Sec–SeOH in either protein or small-molecule systems have remained elusive so far, mostly due to their instability. Here, we report the first direct spectroscopic (1H and 77Se NMR) evidence for the formation of Sec–SeOH in small-molecule selenocysteine and selenopeptide model systems with a cradle-type protective group. The catalytic cycle of GPx was investigated using NMR-observable Sec–SeOH models. All the hitherto proposed chemical processes, i.e., not only those of the canonical catalytic cycle but also those involved in the bypass mechanism, including the intramolecular cyclization of Sec–SeOH to the corresponding five-membered ring selenenyl amide, were examined in a stepwise manner.

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