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.
Ashby
Michael T
MT
Department of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019, USA.
Aneetha
Halikhedkar
H
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