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Eur. J. Mass Spectrom. 3, 396 - 399 (1997)

Letter: Differentiation of isomeric mercapturic acid pathway metabolites of benzo[a]pyrene

Y. Yang, J. Rafter and J.-Å. Gustafsson
Department of Medical Nutrition, Karolinska Institute, Huddinge Hospital F60, NOVUM, S-141 86 Stockholm, Sweden.
J. Sjövall and W.J. Griffiths*
Department of Medical Biochemistry and Biophysics, Karolinska Institute, S-171 77 Stockholm, Sweden.

ABSTRACT:
Isomeric forms of the mercapturic acid pathway metabolites of benzo[a]pyrene (BP) can be differentiated by positive-ion electrospray collision-induced dissociation (CID) mass spectrometry at the nanogram level. The metabolite (+)-r-7,t-8-dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (BPDE), conjugated at position 10 (bay region) with cysteine, fragments to give characteristic ions at m/z 303 corresponding to a BP-triol cation, these ions are not observed in the CID spectra of BPDEs conjugated at position 7 (non-bay region).

Keywords: benzo[a]pyrene, mercapturic acid, metabolites, diolepoxides, electrospray, tandem mass spectrometry, mass spectrometry, N-acetylcysteine.


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