title: [Microbial degradation and 4-chlorophenylacetic acid. Chemical synthesis of 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy- and 4-chloro-2-hydroxyphenylacetic acid (author's transl)].
abstract: Pseudomonas spec. CBS 3 converts 4-chlorophenylacetic acid partly into 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy-, and 4-chloro-2-hydroxyphenylacetic acid by the action of monooxygenases. However, these compounds are not intermediates in the degradation of 4-chlorophenylacetic acid. Pseudomonas spec. CBS 3 is not able to grow with 3-chloro-4-hydroxy- and 4-chloro-3-hydroxyphenylacetic acid as sole carbon source. 4-Chloro-2-hydroxyphenylacetic acid is slowly degraded forming 4-chloro-2,3-dihydroxyphenylacetic acid. The actual degradation of 4-chlorophenylacetic acid seems to be initiated by the attack of a dioxygenase. The syntheses of 4-chloro-3-hydroxyphenylacetic acid and of 4-chloro-2-hydroxyphenylacetic acid are described.
mesh_terms: D007202:Indicators and Reagents; D007700:Kinetics; D013058:Mass Spectrometry; D010648:Phenylacetates / Q000138:chemical synthesis* / Q000378:metabolism*; D011549:Pseudomonas / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
chemical_list: D007202:Indicators and Reagents; D010648:Phenylacetates; C029716:4-chlorophenylacetic acid; C029718:3-chloro-4-hydroxyphenylacetic acid; C029717:4-chloro-3-hydroxyphenylacetic acid; C034468:4-chloro-2-hydroxyphenylacetic acid
vernacular_title: Mikrobieller Abbau von 4-Chlorphenylessigsäure. Chemische Synthese von 3-Chlor-4-hydroxy-, 4-Chlor-3-hydroxy- und 4-Chlor-2-hydroxyphenylessigsäure.