Synthesis and characterization of the selenium analog of glutathione disulfide.
We synthesized the selenium analog of glutathione disulfide by a liquid phase method and named it glutaselenone (i.e., gamma-L-glutamyl-L-selenocysteinylglycine) diselenide. The selenol of selenocysteine was protected by the p-methoxybenzyl group, which was removed by acidolysis with trifluoroacetic acid in the presence of thioanisol. The overall yield of the final product, glutaselenone diselenide, was about 9% based on the starting compound, Se-(p-methoxybenzyl)-L-selenocysteine. Glutaselenone diselenide showed a broad absorption band between 270 and 400 nm and circular dichroism bands around 270 nm (positive) and 330 nm (negative), which were attributable to diselenide bond.
Tamura
T
T
Institute for Chemical Research, Kyoto University, Japan.
Oikawa
T
T
Ohtaka
A
A
Fujii
N
N
Esaki
N
N
Soda
K
K
D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D005978:Glutathione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D016566:Organoselenium Compounds; C079640:glutaselenone diselenide; D005978:Glutathione