Reactive Sulfur Species: Aqueous Chemistry of Sulfenyl Thiocyanates
Authors:
- 29 July 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (33) , 10216-10217
Abstract
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.Keywords
This publication has 15 references indexed in Scilit:
- Reactive Sulfur Species: An Emerging Concept in Oxidative StressBiological Chemistry, 2002
- Formation of Trithiocyanate in the Oxidation of Aqueous ThiocyanateInorganic Chemistry, 2002
- Substrates and products of eosinophil peroxidaseBiochemical Journal, 2001
- Eosinophil Peroxidase Oxidation of ThiocyanateJournal of Biological Chemistry, 2001
- Kinetics and a Revised Mechanism for the Autocatalytic Oxidation of SCN-by ClO2The Journal of Physical Chemistry A, 1999
- Thiocyanate and chloride as competing substrates for myeloperoxidaseBiochemical Journal, 1997
- A Versatile Procedure for the Preparation of Aryl Thiocyanates Using N-Thiocyanatosuccinimide (NTS)Synthetic Communications, 1995
- Steady-state kinetics of thiocyanate oxidation catalyzed by human salivary peroxidaseBiochemistry, 1988
- Mechanism of inactivation of ornithine decarboxylase by α-methylornithineBiochemistry, 1978
- Photodimerization of substituted stilbenesThe Journal of Organic Chemistry, 1970