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The thyroid gland predominantly produces thyroxine or 3,5,3\u2032,5\u2032\u2010tetraiodothyronine (T4) as a prohormone; three isoforms of a mammalian selenoenzyme\u2014iodothyronine deiodinase (DIO1, DIO2 and DIO3)\u2014catalyze the regioselective deiodination of T4 to produce biologically active and inactive metabolites. Whereas DIO1 catalyzes both 5\u2010 and 5\u2032\u2010deiodination of T4, DIO2 and DIO3 selectively mediate 5\u2010 and 5\u2032\u2010deiodination, respectively. In this review we discuss the regioselective deiodination of THs in the presence of organochalcogen compounds. Naphthalene\u2010based compounds containing sulfur and\/or selenium at the <jats:italic>peri<\/jats:italic> positions mediate regioselective 5\u2010deiodination of THs, detailed mechanistic studies having revealed that the heterolytic cleavage of the C\u2212I bond is facilitated by the formation of cooperative Se\/S<jats:bold>\u22c5\u22c5\u22c5<\/jats:bold>I halogen bonds and Se\/S<jats:bold>\u22c5\u22c5\u22c5<\/jats:bold>Se chalcogen bonds. We also discuss the biomimetic deiodination of several TH metabolites, including sulfated THs, iodothyronamines, and iodotyrosines. A brief discussion on the dehalogenation of halogenated nucleosides and nucleobases in the presence of organochalcogen compounds is also included.<\/jats:p>","DOI":"10.1002\/cbic.201900619","type":"journal-article","created":{"date-parts":[[2019,11,26]],"date-time":"2019-11-26T22:10:32Z","timestamp":1574806232000},"page":"911-923","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Halogen Bonding in Biomimetic Deiodination of Thyroid Hormones and their Metabolites and Dehalogenation of Halogenated Nucleosides"],"prefix":"10.1002","volume":"21","author":[{"given":"Santanu","family":"Mondal","sequence":"first","affiliation":[{"name":"Department of Inorganic and Physical Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Debasish","family":"Manna","sequence":"additional","affiliation":[{"name":"Department of Inorganic and Physical Chemistry 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