Document Detail

Reactive sulfur species: aqueous chemistry of sulfenyl thiocyanates.
MedLine Citation:
PMID:  15315413     Owner:  NLM     Status:  MEDLINE    
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.
Michael T Ashby; Halikhedkar Aneetha
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  126     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2004 Aug 
Date Detail:
Created Date:  2004-08-18     Completed Date:  2004-11-09     Revised Date:  2008-01-17    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  10216-7     Citation Subset:  IM    
Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, USA.
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MeSH Terms
Cysteine / chemistry
Glutathione / analogs & derivatives*,  chemistry
Glutathione Disulfide / chemistry
Sulfenic Acids / chemistry*
Sulfhydryl Compounds / chemistry
Thiocyanates / chemistry*
Water / chemistry
Reg. No./Substance:
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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