Alkylation reactions

GSH reacts with alkyl halides via nucleophilic displacement to form sulphides:

If a second, sufficiently reactive halide molecule is reacted with the sulphide, a sulphonium ion can be formed:

Sulphonium ions are reactive toward nucleophiles such as GS-, normally undergoing displacement of a sulphide to yield an alkylated nucleophile:

GS" + G-S+R'R" => G-S-G + R'-S-R"

The most extensively investigated alkylation reaction with glutathione involves halobimanes, because they form the basis for procedures of GSH analysis. Bromoalkyl bimanes are fairly reactive alkyl halides. For example, monobromobimane is 13 times as reactive as benzyl bromide and 43 times as reactive as chlorobimanes toward glutathione. Glutathione derivatives of syn-bimanes are strongly fluorescent and thus applied for glutathione detection accomplished by reverse-phase HPLC analysis (Fahey and Newton 1987, Newton et al. 1981, Anderson 1985).

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