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Arch Microbiol. 1993;160(3):169-78.

Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP 134.

Author information

1
Abteilung Mikrobiologie, Gesellschaft für Biotechnologische Forschung, Braunschweig, Germany.

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.

PMID:
8215795
DOI:
10.1007/bf00249121
[Indexed for MEDLINE]

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