Rule bt0005

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Pattern 4282        All patterns
vic-unsubstituted Aromatic -> vic-Dihydroxyaromatic

Aerobic Likelihood:              Likely

EAWAG-BBD Reaction(s):
1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethylene (DDE) -----> 1,1-Dichloro-2-(dihydroxy-4'-chorophenyl)-2-(4'-chlorophenyl)ethylene (reacID# r0441)
o-Xylene -----> 3,4-Dimethylcatechol (reacID# r1554)
o-Xylene -----> 4,5-Dimethylcatechol (reacID# r1557)

This rule handles the dioxygenation of vic-unsubstituted aromatics (bt0367) and subsequent oxidation to form the catechol derivative (bt0255).When there is more than one potential site of dioxygenation, all possible positions are given. All fused aromatic ring products with hydroxyl at 2,3 position are excluded. The aromatic hydrocarbon dioxygenases produce an activated dioxygen species that is thought to be sufficiently reactive to potentially functionalize most, if not all, aromatic ring carbon atoms (Lipscomb and Hoffman, 2005). Commonly, the position of dioxygenation will be determined by the orientation of the ring(s) in the enzyme's active site, which cannot be predicted. This rule does not act on heterocyclic aromatic rings except for some pyridines, and does not act on many aromatic carboxylates.

bt0042: 1-Nitro-2-unsubstituted aromatic --> vic-Dihydroxyaromatic
bt0055: 1-carboxy-2-unsubstituted Aromatic --> Catechol derivative
bt0065: 1-Amino-2-unsubstituted aromatic --> vic-Dihydroxyaromatic + Amine
bt0072: 1-Carboxy-2-haloaromatic --> 1,2-Dihydroxyaromatic
bt0128: 1-Sulfo-2-unsubstituted aromatic --> vic-Dihydroxyaromatic + Sulfonite
bt0353: mono-carbon-substituted Benzenoid --> 1-substituted-2,3-dihydroxy Benzenoid
bt0374: polynuclear Aromatic system --> 1,2-dioxygenation and cleavage at connecting atom
bt0437: Tetralin derivative --> 1,2-dihydroxytetralin derivative

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Page Author(s): Bo Kyeng Hou, Dave Roe, Michael Turnbull and Rachael Long
August 31, 2010

This is the EAWAG-BBD biotransformation rule, ruleID# bt0005.
It was generated on June 16, 2024 10:10:09 AM CDT.

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