ArticleMolecules (Basel, Switzerland)2023
Demonstration of the Formation of a Selenocysteine Selenenic Acid through Hydrolysis of a Selenocysteine Selenenyl Iodide Utilizing a Protective Molecular Cradle.
Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 3 citations in OpenAlex.
- A Crystalline and Thermally Stable Selenocysteine Selenenic Acid.Angewandte Chemie (International ed. in English) · 2026Article
- Selenoproteins: Minute yet vital players governing cellular fate.Genes & diseases · 2026Review
- Isolable Cysteine Sulfenyl Iodide: Stabilization by a Molecular Cradle, Crystal Structure, and Biologically Relevant Reactivity.Chembiochem : a European journal of chemical biology · 2025Article
- Reusable Selenenyl Iodide-Initiated Cascade Cyclization of Polyenes with N-terminating Groups.Chemistry, an Asian journal · 2025Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Selenocysteine selenenic acids (Sec-SeOHs) and selenocysteine selenenyl iodides (Sec-SeIs) have long been recognized as crucial intermediates in the catalytic cycle of glutathione peroxidase (GPx) and iodothyronine deiodinase (Dio), respectively. However, the observation of these reactive species remained elusive until our recent study, where we successfully stabilized Sec-SeOHs and Sec-SeIs using a protective molecular cradle. Here, we report the first demonstration of the chemical transformation from a Sec-SeI to a Sec-SeOH through alkaline hydrolysis. A stable Sec-SeI derived from a selenocysteine methyl ester was synthesized using the protective cradle, and its structure was determined by crystallographic analysis. The alkaline hydrolysis of the Sec-SeI at -50 °C yielded the corresponding Sec-SeOH in an 89% NMR yield, the formation of which was further confirmed by its reaction with dimedone. The facile and nearly quantitative conversion of the Sec-SeI to the Sec-SeOH not only validates the potential involvement of this process in the catalytic mechanism of Dio, but also highlights its utility as a method for producing a Sec-SeOH.
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Registered trials
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