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

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• 作者：Benjamin D. Reeves ; Jonathan K. Hilmer ; Lisa Mellmann ; Myra Hartzheim ; Kevin Poffenberger ; Keith Johnson ; Neelambari Joshi ; David J. Singel ; Paul A. Grieco
• 关键词：KTALNEWWBGJQRI-UJSQLFKGSA-P
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：16 October, 2013
• 年：2013
• 卷：54
• 期：42
• 页码：5707-5710
• 全文大小：1014 K

文摘

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 PhSO₂Na 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 PhSO₂Na.