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Analysis of mercapturic acid conjugates of xenobiotic compounds using negative ionization and tandem mass spectrometry
Author(s) -
Jones A. Daniel,
Winter Carl K.,
Buonarati Michael H.,
Segall H. J.
Publication year - 1993
Publication title -
biological mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1052-9306
DOI - 10.1002/bms.1200220109
Subject(s) - chemistry , mercapturic acid , mass spectrometry , tandem mass spectrometry , chromatography , fragmentation (computing) , mass spectrum , fast atom bombardment , ion , chemical ionization , ionization , analytical chemistry (journal) , organic chemistry , cysteine , computer science , enzyme , operating system
Mass spectra of mercapturic acid conjugates of two xenobiotic products of lipid peroxidation ( trans ‐4‐hydroxy‐2‐hexenal and trans ‐4‐hydroxy‐2‐nonenal) as well as conjugates of 1,3‐dichloropropene, styrene oxide, 1,2‐naphthalene oxide and α‐chlorotoluene were obtained using fast atom bombardment or negative chemical ionization. Fragmentation pathways were investigated using linked scan and mass‐analyzed ion kinetic energy spectrometric techniques. Characteristics of the spectra obtained using different ionization and sample introduction techniques are compared. Deprotonated molecular ions of mercapturic acids gave simple daughter ion spectra, with the dominant mode of decomposition involving cleavage of CS bonds giving a characteristic neutral loss of 129 Da Screening for mercapturates in urine samples was performed using neutral loss scanning and yielded limits of detection in the low nanogram per milliliter range. Quantitative analysis of the S ‐benzyl mercapturic acid at 1 p.p.b. in urine has been demonstrated using combined gas chromatography/electron capture mass spectrometry with d 3 ‐ S ‐benzyl mercapturic acid as internal standard.