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A comprehensive gas chromatographic/mass spectrometric analysis of 4‐chlorobiphenyl bacterial degradation products
Author(s) -
Massé Robert,
Messier François,
Ayotte Christiane,
Lévesque MarieFrance,
Sylvestre Michel
Publication year - 1989
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200180106
Subject(s) - chemistry , trimethylsilyl , hexanoic acid , metabolite , yield (engineering) , chromatography , biodegradation , catechol , gas chromatography , biotransformation , strain (injury) , organic chemistry , biochemistry , enzyme , medicine , materials science , metallurgy
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 d 9 ‐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.