Reactive sulfur species: aqueous chemistry of sulfenyl thiocyanates.
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.
Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, USA.
Michael T
MT
Ashby
Halikhedkar
H
Aneetha
D003545:Cysteine / Q000737:chemistry; D005978:Glutathione / Q000031:analogs & derivatives* / Q000737:chemistry; D019803:Glutathione Disulfide / Q000737:chemistry; D013434:Sulfenic Acids / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013861:Thiocyanates / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D013434:Sulfenic Acids; D013438:Sulfhydryl Compounds; D013861:Thiocyanates; D014867:Water; D005978:Glutathione; D003545:Cysteine; D019803:Glutathione Disulfide