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Appl Environ Microbiol. 1981 Apr;41(4):942-9. doi: 10.1128/aem.41.4.942-949.1981.

Metabolism of 4-Chloronitrobenzene by the Yeast Rhodosporidium sp.

Applied and environmental microbiology

M D Corbett, B R Corbett

Affiliations

  1. Rosenstiel School of Marine and Atmospheric Science, The University of Miami, Miami, Florida 33149.

PMID: 16345757 PMCID: PMC243838 DOI: 10.1128/aem.41.4.942-949.1981

Abstract

The yeast Rhodosporidium sp. metabolized 4-chloronitrobenzene by a reductive pathway to give 4-chloroacetanilide and 4-chloro-2-hydroxyacetanilide as the major final metabolites. The intermediate production of 4-chloronitrosobenzene, 4-chlorophenylhydroxylamine, and 4-chloroaniline was demonstrated by high-pressure liquid chromatography. Additional studies with selected metabolites established that the metabolite 4-chloro-2-hydroxyacetanilide was produced by an initial Bamberger rearrangement of the hydroxylamine metabolite, followed by acetylation. Direct C hydroxylation of the aromatic ring was not observed in this species. No hydroxamic acid production was detected, even though significant concentrations of the nitroso and hydroxylamine precursors to this functional group were observed.

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