Thionitrite and Perthionitrite in NO Signaling at Zinc
| Autor: | Jeffery A. Bertke, Valiallah Hosseininasab, Timothy H. Warren |
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| Rok vydání: | 2021 |
| Předmět: |
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Molecular chemistry.chemical_classification Tris Molecular Structure chemistry.chemical_element Bioinorganic chemistry General Medicine General Chemistry Zinc Crystallography X-Ray Nitric Oxide Article Catalysis chemistry.chemical_compound chemistry Polymer chemistry Thiol Reactivity (chemistry) Sulfhydryl Compounds Nitrite Boron Nitrites Conjugate |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | NO and H(2)S serve as signaling molecules in biology with intertwined reactivity. HSNO and HSSNO with their conjugate bases (−)SNO and (−)SSNO form in the reaction of H(2)S with NO as well as S-nitrosothiols (RSNO) and nitrite (NO(2)(−)) that serve as NO reservoirs. While the elusive nature of HSNO and HSSNO renders their study challenging, their conjugate bases form isolable zinc complexes (Ph,Me)TpZn(SNO) and (Ph,Me)TpZn(SSNO) supported by tris(pyrazolyl)borate ligands. Reaction of Na(15-C-5)SSNO with (Ph,Me)TpZn(ClO(4)) provides (Ph,Me)TpZn(SSNO) that undergoes S-atom removal by PEt(3) to give (Ph,Me)TpZn(SNO) and S=PEt(3). Unexpectedly stable at room temperature, these Zn-SNO and Zn-SSNO complexes release NO upon heating. (Ph,Me)TpZn(SNO) and (Ph,Me)TpZn(SSNO) quickly react with acidic thiols such as C(6)F(5)SH to form N(2)O and NO, respectively. Increasing the thiol basicity in p-substituted aromatic thiols (4-X)ArSH in the reaction with (Ph,Me)TpZn(SNO) turns on competing S-nitrosation to form (Ph,Me)TpZn-SH and RSNO, the latter a known precursor for NO. |
| Databáze: | OpenAIRE |
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