title: The first direct oxidative conversion of a selenol to a stable selenenic acid: experimental demonstration of three processes included in the catalytic cycle of glutathione peroxidase.
abstract: [structure: see text]. A stable selenenic acid was synthesized by direct oxidation of a selenol bearing a novel bowl-type substituent with H2O2, and its structure was established by X-ray crystallographic analysis. Selenenyl sulfides obtained by the reaction of the selenenic acid with 1,4-dithiols were reduced to the corresponding selenol by treatment with a tertiary amine, thus achieving the experimental demonstration of three processes included in the catalytic cycle of glutathione peroxidase.
authors.affiliation: Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. goto@chem.s.u-tokyo.ac.jp
authors.forename: K
authors.initials: K
authors.lastname: Goto
authors.forename: M
authors.initials: M
authors.lastname: Nagahama
authors.forename: T
authors.initials: T
authors.lastname: Mizushima
authors.forename: K
authors.initials: K
authors.lastname: Shimada
authors.forename: T
authors.initials: T
authors.lastname: Kawashima
authors.forename: R
authors.initials: R
authors.lastname: Okazaki
mesh_terms: D002384:Catalysis; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005979:Glutathione Peroxidase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009112:Muramic Acids / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D009112:Muramic Acids; C442271:N-acetyl-(2-deoxy-2-aminoglucopyranosyl)-(1,4)-N-acetylmuramyl monopeptide; D005979:Glutathione Peroxidase; D005944:Glucosamine