title: Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid.
abstract: A primary-alkyl-substituted selenenyl iodide was successfully synthesized through oxidative iodination of a selenol with N-iodosuccinimide by taking advantage of a cavity-shaped steric protection group. The selenenyl iodide exhibited high thermal stability and remained unchanged upon heating at 100 °C for 3 h in [D₈]toluene. The selenenyl iodide was reduced to the corresponding selenol by treatment with dithiothreitol. Hydrolysis of the selenenyl iodide under alkaline conditions afforded the corresponding selenenic acid almost quantitatively, corroborating the chemical validity of the recent proposal that hydrolysis of a selenenyl iodide to a selenenic acid is potentially involved in the catalytic mechanism of an iodothyronine deiodinase.
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan. ssase@chem.titech.ac.jp.
authors.forename: Shohei
authors.initials: S
authors.lastname: Sase
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan. dolce@m03.itscom.net.
authors.forename: Ryo
authors.initials: R
authors.lastname: Kakimoto
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan. kimura.r.ad@m.titech.ac.jp.
authors.forename: Ryutaro
authors.initials: R
authors.lastname: Kimura
authors.affiliation: Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan. goto@chem.titech.ac.jp.
authors.forename: Kei
authors.initials: K
authors.lastname: Goto
mesh_terms: D002264:Carboxylic Acids / Q000378:metabolism*; D002384:Catalysis; D054879:Halogenation; D006868:Hydrolysis; D007454:Iodides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000378:metabolism*; D010084:Oxidation-Reduction; D018036:Selenium Compounds / Q000737:chemistry*; D013388:Succinimides / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D007454:Iodides; D016566:Organoselenium Compounds; D018036:Selenium Compounds; D013388:Succinimides; C473453:seleninic acid; C442270:selenol; C008155:N-iodosuccinimide
keywords: hydrolysis; iodothyronine deiodinase; kinetic stabilization; selenenic acid; selenenyl iodide