Reaction of thiols with 7-methylbenzopentathiepin.
Polysulfides typically react readily with thiols, thus, reactions of endogenous cellular thiols with the polysulfide linkage in naturally-occuring pentathiepin cytotoxins are likely to be an important aspect of their biological chemistry. Here, it is reported that the reaction of thiols with the pentathiepin ring system initially produces a complex mixture of polysulfides that further decomposes in the presence of excess thiol to yield the corresponding 1,2-benzenedithiol with concomitant production of H(2)S and dimerized thiol. In this reaction, a single molecule of the pentathiepin consumes approximately six equivalents of thiol. The reaction of thiols with the pentathiepin ring system is faster than the analogous reaction involving typical di- and trisulfides.
Chatterji
Tonika
T
Department of Chemistry, University of Missouri-Columbia, MO 65211, USA.
Gates
Kent S
KS
D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000187:drug effects; D005021:Ethylamines / Q000737:chemistry*; D006862:Hydrogen Sulfide / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D013058:Mass Spectrometry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*
C116448:7-methylbenzopentathiepin; D005021:Ethylamines; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D013440:Sulfides; D004247:DNA; D006862:Hydrogen Sulfide