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Synthesis and Characterization of the Selenium Analog of Glutathione Disulfide

✍ Scribed by T. Tamura; T. Oikawa; A. Ohtaka; N. Fujii; N. Esaki; K. Soda

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 290 KB
Volume: 208
Category: Article
ISSN: 0003-2697
DOI: 10.1006/abio.1993.1021

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✦ Synopsis

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.

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