From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway.
Chloroaromatics, a major class of industrial pollutants, may be oxidatively metabolized to chlorocatechols by soil and water microorganisms that have evolved catabolic activities toward these xenobiotics. We show here that 4-chlorocatechol can be further transformed by enzymes of the ubiquitous 3-oxoadipate pathway. However, whereas chloromuconate cycloisomerases catalyze the dechlorination of 3-chloro-cis,cis-muconate to form cis-dienelactone, muconate cycloisomerases catalyze a novel reaction, i.e. the dechlorination and concomitant decarboxylation to form 4-methylenebut-2-en-4-olide (protoanemonin), an ordinarily plant-derived antibiotic that is toxic to microorganisms.
D000272:Adipates / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000378:metabolism*; D002396:Catechols / Q000378:metabolism*; D004463:Ecology; D005663:Furans / Q000378:metabolism*; D019753:Intramolecular Lyases; D007535:Isomerases / Q000502:physiology; D011549:Pseudomonas / Q000378:metabolism
D000272:Adipates; D000900:Anti-Bacterial Agents; D002396:Catechols; D005663:Furans; C027316:3-oxoadipic acid; C037354:protoanemonin; D007535:Isomerases; D019753:Intramolecular Lyases; C021811:muconate cycloisomerase; C038861:4-chlorocatechol