Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism

Bisphenol A (BPA) is metabolized by a Gram-negative aerobic bacterium via a novel pathway involving oxidative skeletal rearrangement of the BPA. Oxidation of the aliphatic methyl group of BPA leads to coproduction of the methyl-hyroxylated 2,2-bis(4-hydroxyphenyl)-1-propanol and a skeletally rearran...

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Bibliographic Details
Published in:The Journal of biological chemistry 1994-03, Vol.269 (10), p.7323-7329
Main Authors: SPIVACK, J, LEIB, T. K, LOBOS, J. H
Format: Article
Language:English
Subjects:
1-Propanol - metabolism
Bacteriology
Benzhydryl Compounds
Binding Sites
Biodegradation, Environmental
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Gram-Negative Anaerobic Bacteria - metabolism
Hydroxylation
Metabolism. Enzymes
Microbiology
Oxidation-Reduction
Phenols - metabolism
Propanols
Stilbenes - metabolism
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Summary:Bisphenol A (BPA) is metabolized by a Gram-negative aerobic bacterium via a novel pathway involving oxidative skeletal rearrangement of the BPA. Oxidation of the aliphatic methyl group of BPA leads to coproduction of the methyl-hyroxylated 2,2-bis(4-hydroxyphenyl)-1-propanol and a skeletally rearranged triol 1,2-bis(4-hydroxyphenyl)-2-propanol. The major route of metabolism (> 80%) is through the rearrangement. The 1,2-bis(4-hydroxyphenyl)-2-propanol is dehydrated to 4,4'-dihydroxy-alpha-methylstilbene, which is rapidly cleaved by oxidation to 4-hydroxybenzaldehyde and 4-hydroxyacetophenone. 4-Hydroxybenzaldehyde is oxidized to 4-hydroxybenzoic acid. Both 4-hydroxybenzoic acid and 4-hydroxyacetophenone are mineralized. The minor product of BPA hydroxylation, 2,2-bis(4-hydroxyphenyl)-1-propanol, is further oxidized to form both 2,2-bis(4-hydroxyphenyl)propanoic acid and a skeletally rearranged tetraol, 2,3-bis(4-hydroxyphenyl)-1,2-propanediol. As is the case in the hydroxylation of BPA, the major product is skeletally rearranged. 2,3-Bis(4-hydroxyphenyl)-1,2-propanediol is slowly transformed to 4-hydroxyphenacyl alcohol.
ISSN:0021-9258
1083-351X
DOI:10.1016/s0021-9258(17)37287-3