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TV-Substituted maleimides which are colored, fluorescent or bifunctional have been widely used as alkylating agents for biologically important thiols.1 ~4) The resulting diastereomers makethe profile of their chromatograms complicated, as shown by Smyth et al.5) This paper describes the separation of the diastereomers of thiol-TVethylmaleimide (NEM) adducts by reverse phase high performance liquid chromatography (HPLC), the !H-NMR assignment of their structures, and some thermodynamic studies of their isomerization.GSH, cysteine (Cys), penicillamine (Pen), or ergothioneine (Erg) was allowed to react with an equimolar quantity ofNEMto give their adducts. The products were separated on the HPLCsystem using an ODScolumn. A fast-moving and a slowly-moving component of the GSH-NEM adducts were rapidly analyzed in D2O on a JEOL FX 100 Spectrometer using sodium 2,2'-dimethyl-2-silapentane-5-sulfonate (DSS) as an external reference.

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