Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid

Shohei Sase; Ryo Kakimoto; Ryutaro Kimura; Kei Goto

doi:10.3390/molecules201219773

Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid

Molecules. 2015 Dec 2;20(12):21415-20. doi: 10.3390/molecules201219773.

Authors

Shohei Sase¹, Ryo Kakimoto², Ryutaro Kimura³, Kei Goto⁴

Affiliations

¹ 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.
² 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.
³ 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.
⁴ 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.

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.

Keywords: hydrolysis; iodothyronine deiodinase; kinetic stabilization; selenenic acid; selenenyl iodide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / metabolism*
Catalysis
Halogenation
Hydrolysis
Iodides / chemical synthesis*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organoselenium Compounds / metabolism*
Oxidation-Reduction
Selenium Compounds / chemistry*
Succinimides / chemistry*

Substances

Carboxylic Acids
Iodides
Organoselenium Compounds
Selenium Compounds
Succinimides
seleninic acid
selenol
N-iodosuccinimide