TheSe-nitrosation in selenoproteins
such as glutathione
peroxidase and thioredoxin reductase to produceSe-nitrososelenocysteines (Sec–SeNOs) has been proposed to play
crucial roles in signaling processes mediated by reactive nitrogen
species and nitrosative-stress responses, although chemical evidence
for the formation of Sec–SeNOs has been elusive not only in
proteins but also in small-molecule systems. Herein, we report the
first synthesis of a Sec–SeNO by employing a selenocysteine
model system that bears a protective molecular cradle. The Sec–SeNO
was characterized using1H and77Se nuclear
magnetic resonance as well as ultraviolet/visible spectroscopy and
found to have persistent stability at room temperature in solution.
The reaction processes involving the Sec–SeNO provide experimental
information that serves as a chemical basis for elucidating the reaction
mechanisms involving the SeNO species in biological functions, as
well as in selenol-catalyzed NO generation fromS-nitrosothiols.