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Selenol Nitrosation and Se ‐Nitrososelenol Homolysis: A Reaction Path with Possible Biochemical Implications
Author(s) -
Wismach Cathleen,
du Mont WolfWalther,
Jones Peter G.,
Ernst Ludger,
Papke Ulrich,
Mugesh Govindasamy,
Kaim Wolfgang,
Wanner Matthias,
Becker Klaus D.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200453872
Subject(s) - nitrosation , homolysis , chemistry , nitrite , in vivo , alkyl , medicinal chemistry , organic chemistry , stereochemistry , radical , biology , nitrate , genetics
The nitrosation of selenol 1 with an alkyl nitrite (see scheme) at −78 °C generated the first Se ‐nitrososelenol 2 , which was identified by IR spectroscopy and further proven by its 1,4‐addition to dimethylbutadiene. Compound 2 decomposes rapidly to give 3 . The experiments may give insight into the interactions of selenoproteins with NO in vivo.