Abstract
2-Chloro-4-methylphenoxyacetate is not a growth substrate for Alcaligenes eutrophus JMP 134 and JMP 1341. It is, however, being transformed by enzymes of 2,4-dichlorophenoxyacetic acid metabolism to 2-chloro-4-methyl-cis, cis-muconate, which is converted by enzymatic 1,4-cycloisomerization to 4-carboxymethyl-2-chloro-4-methylmuconolactone as a dead end metabolite. Chemically, only 3,6-cycloisomerization occurs, giving rise to both diastereomers of 4-carboxychloromethyl-3-methylbut-2-en-4-olide. Those lactones harbonring a chlorosubstituent on the 4-carboxymethyl side chain were surprisingly stable under physiological as well as acidic conditions.
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Pieper, D.H., Stadler-Fritzsche, K., Engesser, KH. et al. Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP 134. Arch. Microbiol. 160, 169–178 (1993). https://doi.org/10.1007/BF00249121
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DOI: https://doi.org/10.1007/BF00249121