NO-Mediated aromatic nitration during decomposition of phenolic S-nitrosothiols in non-aqueous aerobic medium.
Five novel S-nitrosothiol compounds (6-10) derived from L-cysteine were generated in solution and their decomposition rate was followed by UV spectroscopy. In acetonitrile, compounds 9 and 10 were the most stable of this series with a half-life of 24 h. The final organic decomposition products of the five S-nitrosothiols were also analysed. Derivatives 8, 9, and 10, possessing a phenolic hydroxyl group, afforded an unexpected decomposition pathway, with nitration of aromatic ring occurring in non-aqueous media. A mechanism involving a phenoxy radical seems to be implicated.
Petit
C
C
Laboratoire de Synthèse, Physico-Chimie et Radiobiologie, JE-175, Faculté des Sciences Pharmaceutiques, Université Paul Sabatier, Toulouse, France.
Bernardes-Génisson
V
V
Hoffmann
P
P
Souchard
J P
JP
Labidalle
S
S
D000332:Aerobiosis; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D009682:Magnetic Resonance Spectroscopy; D008623:Mercaptoethanol; D009569:Nitric Oxide / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis*; D009603:Nitroso Compounds / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D026403:S-Nitrosothiols; D013056:Spectrophotometry, Ultraviolet
D009574:Nitro Compounds; D009603:Nitroso Compounds; D010636:Phenols; D026403:S-Nitrosothiols; D009569:Nitric Oxide; D008623:Mercaptoethanol; C032635:S-nitrosomercaptoethanol; D003545:Cysteine