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Literature summary for 1.14.13.50 extracted from

  • Rudolph, J.; Erbse, A.H.; Behlen, L.S.; Copley, S.D.
    A radical intermediate in the conversion of pentachlorophenol to tetrachlorohydroquinone by Sphingobium chlorophenolicum (2014), Biochemistry, 53, 6539-6549 .
    View publication on PubMedView publication on EuropePMC

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
pentachlorophenol + NADPH + H+ + O2 Sphingobium chlorophenolicum degradation of pentachlorophenol 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
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Organism

Organism UniProt Comment Textmining
Sphingobium chlorophenolicum P42535
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
pentachlorophenol + NADPH + H+ + O2 degradation of pentachlorophenol Sphingobium chlorophenolicum 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
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pentachlorophenol + NADPH + H+ + O2 the enzyme is an unusually slow flavin-dependent monooxygenase (kcat = 0.02/s) that converts pentachlorophenol to a highly reactive product, tetrachlorobenzoquinone. By stopped-flow spectroscopy, it is shown that the steps up to and including formation of tetrachlorobenzoquinone are rapid (5-30/s). Before products can be released from the active site, the strongly oxidizing tetrachlorobenzoquinone abstracts an electron from a donor at the active site, possibly a cysteine residue, resulting in an off-pathway diradical state that only slowly reverts to an intermediate capable of completing the catalytic cycle Sphingobium chlorophenolicum 2,3,5,6-tetrachloro-1,4-benzoquinone + NADP+ + chloride + H2O
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Synonyms

Synonyms Comment Organism
PCP hydroxylase
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Sphingobium chlorophenolicum
pentachlorophenol hydroxylase
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Sphingobium chlorophenolicum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.02
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Pentachlorophenol pH 7.0, 22°C Sphingobium chlorophenolicum

Cofactor

Cofactor Comment Organism Structure
FAD flavoprotein Sphingobium chlorophenolicum

General Information

General Information Comment Organism
metabolism degradation of pentachlorophenol Sphingobium chlorophenolicum