Metabolism of arylsulphonates by micro-organisms.
1. Species of Pseudomonas capable of degrading arylsulphonates and detergents of the alkylbenzenesulphonate type were isolated from sewage and river water. 2. Benzenesulphinate, benzenesulphonate and toluene-p-sulphonate were rapidly degraded by these organisms with the release of the sulphonate group as sulphite; detergent homologues with a chain length up to 16 carbon atoms (4-n-hexadecyl-benzenesulphonate) also released sulphite. Sulphite oxidation to sulphate in the medium can occur non-enzymically. 3. Growth on benzenesulphonate and toluene-p-sulphonate elicited a catechol 2,3-oxygenase, which effected a ;meta' cleavage of the ring. The metabolic route for benzenesulphonate was determined as: benzenesulphonate-->catechol-->2-hydroxymuconic semialdehyde-->formate and 4-hydroxy-2-oxovalerate-->acetaldehyde and pyruvate; the enzymes catalysing these steps were all inducible. 4. Toluene-p-sulphonate was degraded via 2-hydroxy-5-methylmuconic semialdehyde to formate and 4-hydroxy-2-oxohexanoate and the latter was cleaved to propionaldehyde and pyruvate. Propionaldehyde and propionate were oxidized rapidly by toluene-p-sulphonate-grown cells but slowly by fumarate-grown organisms. 5. The specificity of the catechol 2,3-oxygenase induced by the arylsulphonates, towards catechol and the methylcatechols, varied during the purification and suggested that 3-methylcatechol was probably oxidized by a separate enzyme. Detergents of the alkylbenzenesulphonate type also induced a catechol 2,3-oxygenase in these bacteria. 6. A few isolates, after growth on benzenesulphonate, opened the ring of catechol by an ;ortho' route to form cis-cis-muconate. The enzymes to degrade this intermediate to beta-oxoadipate were also present in induced cells.
D000079:Acetaldehyde / Q000378:metabolism; D002247:Carbon Isotopes; D002396:Catechols / Q000378:metabolism; D002474:Cell-Free System; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D003902:Detergents / Q000378:metabolism*; D004790:Enzyme Induction; D005561:Formates / Q000378:metabolism; D010105:Oxygenases / Q000378:metabolism; D011422:Propionates / Q000378:metabolism; D011549:Pseudomonas / Q000378:metabolism*; D011773:Pyruvates / Q000378:metabolism; D013053:Spectrophotometry; D013447:Sulfites / Q000378:metabolism; D013451:Sulfonic Acids / Q000378:metabolism*; D014050:Toluene / Q000378:metabolism; D014465:Ultrasonics
D002247:Carbon Isotopes; D002396:Catechols; D003902:Detergents; D005561:Formates; D011422:Propionates; D011773:Pyruvates; D013447:Sulfites; D013451:Sulfonic Acids; D014050:Toluene; D010105:Oxygenases; D000079:Acetaldehyde