Bacterial degradation of 4-hydroxyphenylacetic acid and homoprotocatechuic acid.
A species of Acinetobacter and two strains of Pseudomonas putida when grown with 4-hydroxyphenylacetic acid gave cell extracts that converted 3,4-dihydroxyphenylacetic acid (homoprotocatechuic acid) into carbon dioxide, pyruvate, and succinate. The sequence of enzyme-catalyzed steps was as follows: ring-fission by a 2,3-dioxygenase, nicotinamide adenine dinucleotide-dependent dehydrogenation, decarboxylation, hydration, aldol fission, and oxidation of succinic semialdehyde. Two new metabolites, 5-carboxymethyl-2-hydroxymuconic acid and 2-hydroxyhepta-2,4-diene-1,7-dioic acid, were isolated from reaction mixtures and a third, 4-hydroxy-2-ketopimelic acid, was shown to be cleaved by extracts to give pyruvate and succinic semialdehyde. Enzymes of this metabolic pathway were present in Acinetobacter grown with 4-hydroxyphenylacetic acid but were effectively absent when 3-hydroxyphenylacetic acid or phenylacetic acid served as sources of carbon.
D000150:Acinetobacter / Q000201:enzymology / Q000378:metabolism*; D000421:Alcaligenes / Q000378:metabolism*; D000445:Aldehyde Oxidoreductases / Q000378:metabolism; D001565:Benzoates / Q000378:metabolism*; D001673:Biodegradation, Environmental; D002245:Carbon Dioxide / Q000096:biosynthesis; D002458:Cell Fractionation; D002474:Cell-Free System; D002849:Chromatography, Gas; D003653:Decarboxylation; D005634:Fructose-Bisphosphate Aldolase / Q000378:metabolism; D007700:Kinetics; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism; D010105:Oxygenases / Q000378:metabolism; D010648:Phenylacetates / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology / Q000378:metabolism*; D011773:Pyruvates / Q000096:biosynthesis; D013056:Spectrophotometry, Ultraviolet; D013386:Succinates / Q000096:biosynthesis
D001565:Benzoates; D010648:Phenylacetates; D011773:Pyruvates; D013386:Succinates; D002245:Carbon Dioxide; D010088:Oxidoreductases; D010105:Oxygenases; D000445:Aldehyde Oxidoreductases; D005634:Fructose-Bisphosphate Aldolase