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Selective trapping of SNO-BSA and GSNO by benzenesulfinic acid sodium salt: mechanistic study of thiosulphonate formation and feasibility as a protein S-nitrosothiol detection strategy.


ABSTRACT: The conversion of S-nitrosothiols to thiosulphonates 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 PhSO2Na and RSNO) have been determined under mild acidic conditions (pH 4.0). The products have been identified as the corresponding thiosulphonates (GSSO2Ph and BSA-SSO2Ph) along with PhSO2NHOH obtained in a 1:1 ratio. GSH, GSSG, and BSA were unreactive to PhSO2Na.

SUBMITTER: Reeves BD 

PROVIDER: S-EPMC3811913 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Selective trapping of SNO-BSA and GSNO by benzenesulfinic acid sodium salt: mechanistic study of thiosulphonate formation and feasibility as a protein <i>S</i>-nitrosothiol detection strategy.

Reeves Benjamin D BD   Hilmer Jonathan K JK   Mellmann Lisa L   Hartzheim Myra M   Poffenberger Kevin K   Johnson Keith K   Joshi Neelambari N   Singel David J DJ   Grieco Paul A PA  

Tetrahedron letters 20131001 42


The conversion of <i>S</i>-nitrosothiols to thiosulphonates by reaction with the sodium salt of benzenesulfinic acid (PhSO<sub>2</sub>Na) has been examined in detail with the exemplary substrates <i>S</i>-nitrosoglutathione (GSNO) and <i>S</i>-nitrosylated bovine serum albumin (SNO-BSA). The reaction stoichiometry (2:1, PhSO<sub>2</sub>Na:RSNO) and the rate law (first order in both PhSO<sub>2</sub>Na and RSNO) have been determined under mild acidic conditions (pH 4.0). The products have been ide  ...[more]

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