| Reactive sulfur species: aqueous chemistry of sulfenyl thiocyanates. | |
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MedLine Citation:
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PMID: 15315413 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Sulfenyl thiocyanate (RSSCN) derivatives of penicillamine (PENSCN) and glutathione (GSSCN) have been synthesized in situ at pH = 0 from equilibrium mixtures that consists of hypothiocyanous acid (HOSCN), thiocyanogen ((SCN)2), and trithiocyanate ((SCN)3-). The electrophilic thiocyanating agent N-thiocyanatosuccinimide (NTS) also reacts with PEN and GSH to yield the corresponding RSSCN derivatives. PENSCN and GSSCN were characterized by NMR, ES-MS, and IR spectroscopy. While stable at pH = 0, at higher pH the RSSCN derivatives decompose to give products that are consistent with hydrolysis and formation of reactive sulfenic acids. |
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Authors:
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Michael T Ashby; Halikhedkar Aneetha |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 126 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2004 Aug |
Date Detail:
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Created Date: 2004-08-18 Completed Date: 2004-11-09 Revised Date: 2008-01-17 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 10216-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cysteine
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chemistry Glutathione / analogs & derivatives*, chemistry Glutathione Disulfide / chemistry Sulfenic Acids / chemistry* Sulfhydryl Compounds / chemistry Thiocyanates / chemistry* Water / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Sulfenic Acids; 0/Sulfhydryl Compounds; 0/Thiocyanates; 27025-41-8/Glutathione Disulfide; 52-90-4/Cysteine; 70-18-8/Glutathione; 7732-18-5/Water |
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