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. 1994 May;60(5):1658–1662. doi: 10.1128/aem.60.5.1658-1662.1994

Evidence for Chlorine Migration during Oxidation of 2-Chlorobiphenyl by a Type II Methanotroph

P Adriaens 1,*
PMCID: PMC201533  PMID: 16349261

Abstract

Axenic methanotrophic culture strain CSC1, which was derived from a mixed-culture aquifer sample, oxidized 2-chlorobiphenyl to a hydroxylated chlorobiphenyl intermediate identified as 2-hydroxy-3-chlorobiphenyl. Minor amounts of another hydroxylated chlorobiphenyl isomer, assumed to be the nonmigrated product 3-hydroxy-2-chlorobiphenyl, were found in axenic culture incubation extracts. The occurrence of chlorine migration during oxidation indicates that the metabolite is formed via a concerted oxidation mechanism involving an arene oxide, which rearranges spontaneously to the hydroxylated intermediate via an NIH shift mechanism.

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Selected References

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