title: Microbial metabolism of alkylbenzene sulphonates. Bacterial metabolism of undecylbenzene-p-sulphonate and dodecylbenzene-p-sulphonate.
abstract: 1. A study was made of the biodegradation of alkylbenzene sulphonate homologues, one of the major components of commercially marketed detergents. A Bacillus species was elected for growth on alkylbenzene sulphonate homologues as the sole source of carbon and sulphur. 2. The results from both whole-cell and cell-free systems indicated that the alkyl, aryl and sulphonate moieties of alkylbenzene sulphonate homologues were all further metabolized by the Bacillus species. 3. The alkyl side chain, after a presumed initial oxidation of the terminal methyl group, was subsequently oxidized by a beta-oxidation pathway. Three enzymes of the beta-oxidation pathway, i.e. acyl-CoA synthetase, acyl-CoA dehydrogenase and beta-hydroxyacyl-CoA dehydrogenase, were identified in cell-free extracts of the detergent-grown Bacillus species. The substrate specificity of acyl-CoA synthetase indicated activity towards several alkylbenzene sulphonate homologues. 4. The sulphonate moiety was released as sulphite by a desulphonating enzyme. Some kinetic properties of this enzyme were determined. The sulphite was subsequently metabolized to either sulphate or adenosine 5'-sulphatophosphate. Two enzymes involved in sulphite metabolism, i.e. sulphite-cytochrome c reductase and adenosine 5'-sulphatophosphate-cytochrome c reductase were detected in cell-free extracts of undecylbenzene-p-sulphonate-grown Bacillus species. 5. The combined results of continuous sampling programmes monitored by both t.l.c. and sulphite appearance in the growth medium indicated that desulphonation of the aromatic moiety was the likely first step in the overall biodegradation of several alkylbenzene sulphonate homologues. 6. The presence of p-hydroxyphenylpropionate, p-hydroxybenzoate and 3,4-dihydroxybenzoate in cells after growth on several alkylbenzene sulphonate homologues containing an odd number of carbon atoms in the side chain was confirmed by g.l.c. and t.l.c. analysis. Cells grown on several homologues containing an even number of carbon atoms in the side chain were shown to contain p-hydroxyphenylacetate and 3,4-dihydroxyphenylacetate. 7. The aromatic nucleus obtained from undecylbenzene-p-sulphonate was further metabolized by an oxidation sequence involving an ;ortho-cleavage' route. 8. An overall metabolic pathway for the biodegradation of various alkylbenzene sulphonate homologues by this Bacillus species is proposed.
mesh_terms: D000227:Adenine Nucleotides / Q000378:metabolism; D000473:Alkanes / Q000378:metabolism; D001407:Bacillus / Q000378:metabolism*; D001555:Benzene Derivatives / Q000378:metabolism*; D001565:Benzoates; D001711:Biotransformation; D002264:Carboxylic Acids / Q000378:metabolism; D002474:Cell-Free System; D002855:Chromatography, Thin Layer; D003065:Coenzyme A; D003066:Coenzyme A Ligases; D003574:Cytochrome c Group; D003902:Detergents; D007700:Kinetics; D010084:Oxidation-Reduction; D010088:Oxidoreductases; D011422:Propionates; D013424:Sulfanilamides / Q000378:metabolism; D013447:Sulfites / Q000378:metabolism; D013451:Sulfonic Acids / Q000378:metabolism*
chemical_list: D000227:Adenine Nucleotides; D000473:Alkanes; D001555:Benzene Derivatives; D001565:Benzoates; D002264:Carboxylic Acids; D003574:Cytochrome c Group; D003902:Detergents; D011422:Propionates; D013424:Sulfanilamides; D013447:Sulfites; D013451:Sulfonic Acids; D010088:Oxidoreductases; D003066:Coenzyme A Ligases; D003065:Coenzyme A