Chatterji Tonika, Gates Kent S
Department of Chemistry, University of Missouri-Columbia, MO 65211, USA.
Bioorg Med Chem Lett. 2003 Apr 7;13(7):1349-52. doi: 10.1016/s0960-894x(03)00103-3.
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.
多硫化物通常很容易与硫醇发生反应，因此，内源性细胞硫醇与天然存在的五硫杂环辛毒素中的多硫键发生反应很可能是其生物化学的一个重要方面。在此报道，硫醇与五硫杂环辛环系统的反应最初会产生多硫化物的复杂混合物，在过量硫醇存在下，该混合物会进一步分解，生成相应的1,2 - 苯二硫醇，并伴随产生H₂S和二聚硫醇。在该反应中，单个五硫杂环辛分子消耗约六个当量的硫醇。硫醇与五硫杂环辛环系统的反应比涉及典型二硫化物和三硫化物的类似反应更快。
