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.
[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.
Goto
K
K
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
Nagahama
M
M
Mizushima
T
T
Shimada
K
K
Kawashima
T
T
Okazaki
R
R
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
D009112:Muramic Acids; C442271:N-acetyl-(2-deoxy-2-aminoglucopyranosyl)-(1,4)-N-acetylmuramyl monopeptide; D005979:Glutathione Peroxidase; D005944:Glucosamine