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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Liaw, Wen-feng Tsou, Chih-chin |
| Description | Author Affiliation: Tsou CC ( Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.) |
| Abstract | S-Nitrosation of the coordinated thiolate of dinitrosyl iron complexes (DNICs) to generate S-nitrosothiols (RSNOs) was demonstrated. Transformation of $[\{(NO)_{2}Fe(μ-StBu)\}_{2}]$ (1-tBuS) into the $\{Fe(NO)_{2}\}^{9}$ DNIC $[(NO)_{2}Fe(StBu)(MeIm)]$ (2-MeIm) occurs under addition of 20 equiv of 1-methylimidazole (MeIm) into a solution of 1-tBuS in THF. The dynamic interconversion between $\{Fe(NO)_{2}\}^{9}$ $[(NO)_{2}Fe(S-NAP)(dmso)]$ (2-dmso) (NAP=N-acetyl-D-penicillamine) and $[\{(NO)_{2}Fe(μ-S-NAP)\}_{2}]$ (1-NAP) was also observed in a solution of complex 1-NAP in DMSO. In contrast to the reaction of complex 2-MeIm and bis(dimethylthiocarbamoyl) disulfide $((DTC)_{2})$ to yield $\{Fe(NO)\}^{7}$ $[(NO)Fe(DTC)_{2}]$ (3) $(DTC=S_{2}CNMe_{2})$ accompanied by $(tBuS)_{2}$ and $NO_{(g)},$ transformation of $\{Fe(NO)_{2}\}^{9}2-MeIm$ (2-dmso) into RSNOs (RS=tBuS, NAP-S) along with complex 3 induced by the Brønsted acid solution of $(DTC)_{2}$ demonstrated that Brønsted acid may play a critical role in triggering S-nitrosation of the coordinated thiolate of DNICs 2-MeIm (or 2-dmso) to produce RSNOs. That is, DNIC-mediated S-nitrosation requires a Brønsted acid–Lewis base pair to produce RSNO. Transformation of DNICs into RSNOs may only occur on the one-thiolate-containing $\{Fe(NO)_{2}\}^{9}$ DNICs, in contrast to protonation of the two-thiolate-containing DNICs $[(NO)_{2}Fe(SR)_{2}]^{−}$ by Brønsted acid to yield $[\{(NO)_{2}Fe(μ-SR)\}_{2}].$ These results might rationalize that the known protein-Cys-SNO sites derived from DNICs were located adjacent to acid and base motifs, and no protein-bound SNO characterized to date has been directly derived from $[protein–(cysteine)_{2}Fe(NO)_{2}]$ in biology. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 47 |
| Volume Number | 17 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2011-11-18 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry Nitrogen Oxides S-Nitrosothiols Acid-Base Equilibrium Electron Spin Resonance Spectroscopy Imidazoles Ligands Molecular Structure Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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