Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes Eutrophus JMP 134

Overview

Journal Arch Microbiol

Specialty Microbiology

Date 1993 Jan 1

PMID 8215795

Citations 14

Authors

D H Pieper

K Stadler-Fritzsche

K H Engesser

H J Knackmuss

Affiliations

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Abstract

2-Chloro-4-methylphenoxyacetate is not a growth substrate for Alcaligenes eutrophus JMP 134 and JMP 134-1. 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 harboring a chlorosubstituent on the 4-carboxymethyl side chain were surprisingly stable under physiological as well as acidic conditions.

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