title: Synthesis and characterization ofSe-adenosyl-L-selenohomocysteine selenoxide.
abstract: Selenium is an essential micronutrient in humans due to the important roles of the selenocysteine-containing selenoproteins. Organoselenium metabolites are generally found to be substrates for the biochemical pathways of their sulfur analogs, and the redox chemistry of selenomethionine and some other metabolites have been previously reported. We now report the first synthesis and characterization ofSe-adenosylselenohomocysteine selenoxide (SeAHO) prepared via hydrogen peroxide oxidation ofSe-adenosylselenohomocysteine (SeAH). The selenoxide SeAHO, in contrast to its corresponding sulfoxideS-adenosylhomocysteine (SAHO), can form hydrate, has an electrostatic interaction between the α-amino acid moiety and the highly polar selenoxide functional group, and readily oxidizes glutathione (GSH) and cysteine thiols.
authors.affiliation: Department of Pharmaceutical Sciences, 140 The Fenway Bldg., Room 206, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115-5000, Tel: +1 617 373 3163.
authors.forename: Richard I
authors.initials: RI
authors.lastname: Duclos
authors.affiliation: Department of Chemistry and Chemical Biology, Hurtig Hall, Room 102, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115-5000, Tel: +1 617 373 2800.
authors.forename: Dillon C
authors.initials: DC
authors.lastname: Cleary
authors.affiliation: Department of Chemistry and Chemical Biology, Hurtig Hall, Room 102, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115-5000, Tel: +1 617 373 2800.
authors.forename: Kalli C
authors.initials: KC
authors.lastname: Catcott
authors.affiliation: Department of Chemistry and Chemical Biology, Hurtig Hall, Room 102, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115-5000, Tel: +1 617 373 2800.
authors.forename: Zhaohui Sunny
authors.initials: ZS
authors.lastname: Zhou
keywords: Se-adenosylselenohomocysteine; Se-adenosylselenohomocysteine selenoxide; organoselenium; oxidation; selenomethionine