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Formation of N-Ethylmaleimide (NEM)-Glutathione Conjugate and N-Ethylmaleamic Acid Revealed by Mass Spectral Characterization of Intracellular and Extracellular Microbial Metabolites of NEM

Department of Chemistry, Natural Sciences Complex, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000

Received 25 June 2007/ Accepted 22 October 2007

The extracellular and intracellular metabolites formed upon exposure of activated sludge microorganisms to a sublethal concentration of N-ethylmaleimide were monitored by liquid chromatography with ion trap mass spectrometry. The metabolite N-ethylsuccinimido-S-glutathione (m/z 433) was converted rapidly to N-(2-oxoethyl)-2,2-(propionylamino)propanamide (m/z 187) and N-ethylmaleamic acid (m/z 144).

Published ahead of print on 2 November 2007.