599-71-3Relevant articles and documents
Selective trapping of SNO-BSA and GSNO by benzenesulfinic acid sodium salt: Mechanistic study of thiosulfonate formation and feasibility as a protein S-nitrosothiol detection strategy
Reeves, Benjamin D.,Hilmer, Jonathan K.,Mellmann, Lisa,Hartzheim, Myra,Poffenberger, Kevin,Johnson, Keith,Joshi, Neelambari,Singel, David J.,Grieco, Paul A.
, p. 5707 - 5710 (2013)
The conversion of S-nitrosothiols to thiosulfonates by reaction with the sodium salt of benzenesulfinic acid (PhSO2Na) has been examined in detail with the exemplary substrates S-nitrosoglutathione (GSNO) and S-nitrosylated bovine serum albumin (SNO-BSA). The reaction stoichiometry (2:1, PhSO2Na:RSNO) and the rate law (first order in both PhSO 2Na and RSNO) have been determined under mild acidic conditions (pH 4.0). The products have been identified as the corresponding thiosulfonates (GSSO2Ph and BSA-SSO2Ph) along with PhSO2NHOH obtained in a 1:1 ratio. GSH, GSSG, and BSA were unreactive to PhSO 2Na.
Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger
Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.
, p. 1745 - 1755 (2018/04/17)
A new family of photoactivatable HNO donors of general structure RSO2NHO-PT [where PT represents the (3-hydroxy-2-naphthalenyl)methyl (3,2-HMN) phototrigger] has been developed, which rapidly releases HNO. Photogeneration of HNO was demonstrated using the vitamin B12 derivative aquacobalamin as a trapping agent. The amount of sulfonate RSO2– produced was essentially the same as the amount of HNO released upon photolysis, providing a convenient method to indirectly quantify HNO release. Two competing pathways were also observed; a pathway involving O–N bond cleavage leading to release of a sulfonamide, and a pathway resulting in release of the parent Nhydroxysulfonamide RSO2NHOH (for HNO donors with Me- and Ph-containing leaving groups only). Up to approximately 70 % of the HNO-generating pathway was observed with the CF3-containing leaving group, with HNO generation favored for small percentages of aqueous buffer in the acetonitrile/pH 7.00 phosphate buffer solvent mixture. Characterization of the photoproducts obtained from steady-state irradiation by NMR spectroscopy showed that the desired HNO-generating pathway was less favored for HNO donors with Me- and Ph-containing leaving groups compared to the CF3-containing leaving group, suggesting that the excellent CF3-containing leaving group promotes HNO generation.
Nondirected, cu-catalyzed sp3 C-H aminations with hydroxylamine-based amination reagents: Catalytic and mechanistic studies
Wang, Anqi,Venditto, Nicholas J.,Darcy, Julia W.,Emmert, Marion H.
supporting information, p. 1259 - 1268 (2017/05/29)
This work demonstrates the use of hydroxylamine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.
Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones
Banerjee, Ranjan,Bruce King
supporting information; experimental part, p. 4580 - 4583 (2009/12/09)
Treatment of cyclobutanone or cyclopentanone with N- hydroxybenzenesulfonamide under basic conditions yields the ring-expanded cyclic hydroxamic acid in 18-69% yield. Reactions of substituted cyclobutanones give ring expanded products where the -NOH group regio- and stereoselectively inserts to the more substituted position. This expansion likely proceeds through a mechanism that includes addition of the N-anion of N-hydroxybenzenesulfonamide to the ketone and a C-nitroso intermediate that rearranges to the final product.
REACTION OF HYDROXYLAMINE WITH BENZENESULFONYL CHLORIDE. X-RAY CRYSTAL STRUCTURE OF PILOTY'S ACID AND OTHER BENZENESULFONYLHYDROXYLAMINES.
Scholz, John N.,Engel, Paul S.,Glidewell, Christopher,Whitmire, Kenton H.
, p. 7695 - 7708 (2007/10/02)
The X-ray crystal structures of the four stable phenylhydroxylamines (PhSO2NHOH, (PhSO2)2NOH, PhSO2NHOSO2Ph, (PhSO2)2NOSO2Ph), and of PhSO3-+H3NHNSO2Ph are presented.The last of these is a by-product obtained during the isolation of PhSO2NHOH (Piloty's Acid).The formation of and the bonding in these molecules are discussed.
