Chemical structure and biodegradability of halogenated aromatic compounds. Conversion of chlorinated muconic acids into maleoylacetic acid

Biochem J. 1980 Oct 15;192(1):339-47. doi: 10.1042/bj1920339.

Abstract

1. An enzyme for the cycloisomerization of 2- and 3-chloro-cis,cis-muconic acid was isolated from 3-chlorobenzoate-grown cells of Pseudomonas sp. B13. It was named muconate cycloisomerase II, because it could it clearly be differentiated by its Km and Vmax. values from an ordinary muconate cycloisomerase, which functioned in benzoate catabolism and exhibited low activity with the chlorinated substrates. 2-Chloro-cis,cis-muconic acid was converted into trans- and 3-chloro-cis,cis--muconic acid into cis-4-carboxymethylenebut-2-en-4-olide together with dehalogenation. 2. An enzyme was isolated from chlorobenzoate-grown cells, which converted the 4-carboxymethylenebut-2-en-4-olides into maleoylacetic acid.

MeSH terms

  • Biodegradation, Environmental
  • Carboxylic Ester Hydrolases / isolation & purification
  • Chemical Phenomena
  • Chemistry
  • Chromatography, Gel
  • Cyclization
  • Dicarboxylic Acids / isolation & purification
  • Hydrocarbons, Halogenated* / metabolism
  • Intramolecular Lyases*
  • Isomerases / isolation & purification
  • Kinetics
  • Maleates* / metabolism
  • Pseudomonas / enzymology
  • Sorbic Acid / analogs & derivatives
  • Sorbic Acid / isolation & purification

Substances

  • Dicarboxylic Acids
  • Hydrocarbons, Halogenated
  • Maleates
  • maleoylacetic acid
  • Carboxylic Ester Hydrolases
  • 3-oxoadipate enol-lactonase
  • Isomerases
  • Intramolecular Lyases
  • muconate cycloisomerase
  • Sorbic Acid