Rule bt0351

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Pattern 2780        All patterns
vic-Dihydroxybenzenoid -> 2-Oxopent-4-enoate derivative + Carboxylate
1-Amino-2-hydroxybenzenoid -> 2-Amino-2,4-dienoate derivate + Carboxylate

Aerobic Likelihood:              Likely

EAWAG-BBD Reaction(s):
4-iso-Propylcatechol -----> Pyruvate + 3-Methyl-2-butanone (reacID# r1728)

This rule handles extradiol (meta) ring cleavage for vic-dihydroxybenzenoids and 1-amino-2-hydroxybenzenoids, including, but not limited to, 2,3-dihydroxybiphenyl derivatives, many PCB congeners (Pieper, 2005), 3- and 4-substituted chlorocatechols, 2-aminophenol, 2,3-dihydroxy DDT and its derivatives, 3- and 4-substituted alkyl catechols, diphenylether derivatives, and aromatized intermediates of steroid degradation (e.g., testosterone). It includes extradiol ring cleavage of vic-dihydroxybenzenoids (bt0008) and distal ring cleavage of 1-amino-2-hydroxybenzenoids (bt0041) to form 2-hydroxymuconate semialdehyde and 2-aminomuconate semialdehyde derivatives, respectively. 2-Aminomuconate semialdehyde derivatives undergoes hydrolytic deamination (bt0032) to form the 2-hydroxymuconate semialdehyde product. 3-Carboxyl catechols, such as 2,3-dihydroxy-p-cumate, undergo decarboxylation of the 3-carboxy group following meta cleavage. Hydrolysis of the C5-C6 bond (bt0040), or oxidation of the aldehyde to a carboxylate (bt0003), followed by decarboxylation (bt0051), produces a 2-amino-2,4-dienoate derivative or an enol product, which quickly tautomerizes to a 2-oxopent-4-enoate derivative. 2,3-Dihydroxybiphenyl derivatives are only cleaved at the side closest to the second phenyl ring. Rings are not cleaved next to the halogenated carbon in 3-halocatechol substrates. If the catechol substrate is not symmetric and its cleavage site preference is unknown, the compound is cleaved on both sides of the vic-dihydroxyl group.

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Page Author(s): Michael Turnbull
September 09, 2010

This is the EAWAG-BBD biotransformation rule, ruleID# bt0351.
It was generated on September 19, 2017 6:34:12 AM CDT.

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