1. From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway
- Author
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Dietmar H. Pieper, Rolf-Michael Wittich, Kenneth N. Timmis, Megharaj Mallavarapu, Rafael Blasco, Blasco, R, Wittich, RM, Timmis, KN, and Pieper, DH
- Subjects
chemistry.chemical_classification ,Ecology ,Catabolism ,Decarboxylation ,Stereochemistry ,Adipates ,Microorganism ,Catechols ,Cell Biology ,Biochemistry ,Anti-Bacterial Agents ,chemistry.chemical_compound ,Enzyme ,chemistry ,Pseudomonas ,Antibiotic formation ,Furans ,Intramolecular Lyases ,Isomerases ,Xenobiotic ,Molecular Biology ,Protoanemonin - Abstract
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.