S

Thioacyl halide

Figure 25 Examples of glutathione conjugation by nucleophilic substitution involving activated alkyl moieties (80; X = halogen, -OSO3H), melphalan (81) and other alkylating cytostatic drugs (for which chloride elimination does not depend on the presence of GSH), adequately substituted aromatic rings (84; X = halogen, nitro, sulfoxide, sulfone), acyl halides (85; X = F, Cl, Br) and acyl-glucuronides (85; X = O-Gluc), and haloalkenes (86). Note that two mechanisms of GSH conjugation exist for haloalkenes, namely substitution (producing conjugates 87) and addition (producing conjugates 88); both routes then lead to highly reactive metabolites such as thioacyl halides and thioketenes.

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