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A comprehensive gas chromatographic/mass spectrometric analysis of 4-chlorobiphenyl bacterial degradation products

1989; Wiley; Volume: 18; Issue: 1 Linguagem: Inglês

10.1002/bms.1200180106

2376-3868

Robert Massé, François Messier, Christiane Ayotte, M.-J. Lévesque, Michel Sylvestre,

Analytical Chemistry and Chromatography

Bacterial metabolism of 4-chlorobiphenyl (4-CB), a model compound of polychlorinated biphenyls, has been investigated. Grown in the presence of 4-CB, Gram-negative strain B-206 oxidized the non-chlorinated ring to yield 2,3-dihydroxy-2,3-dihydro-4′-chlorobiphenyl, 3,4-dihydroxy-3,4-dihydro-4′-chlorobiphenyl, as well as their corresponding 2,3 and 3,4 catechol analogues, 2-hydroxy-4′-chlorobiphenyl and 4-hydroxy-4′-chlorobiphenyl. The intermediate catechols were further oxidized to yield 2-hydroxy-6-oxo-6-(4′-chlorophenyl)-hexa-2,4-dienoic acid, 2-hydroxy-6-oxo-(4′-chlorophenyl)-hexanoic acid, 5-oxo-5-(4′-chlorophenyl)-pentanoic acid, 4-oxo-4-(4′-chlorophenyl)-butanoic acid, 4-chlorocinnamic acid and 4-chlorobenzoic acid, which accumulates in the culture broths. The hydroxylated biotransformation products were characterized by gas chromatographic/mass spectrometric analysis as trimethylsilyl (TMS) and d9-TMS derivatives, whereas metabolites with vicinal diols were also analysed as their n-butylboronate derivatives. Gas chromatographic/mass spectrometric features of the metabolite derivatives are presented and 4-CB biodegradation pathways are discussed.