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

Archives of microbiology ·Vol. 160 ·No. 3 ·1993-00-00 ·Pages 169-78

Pieper DH, Stadler-Fritzsche K, Engesser KH, Knackmuss HJ

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.

MeSH Terms

2,4-Dichlorophenoxyacetic Acid/metabolism 2-Methyl-4-chlorophenoxyacetic Acid/chemistry,metabolism Alcaligenes/metabolism Biodegradation, Environmental Magnetic Resonance Spectroscopy Molecular Structure Stereoisomerism

Chemicals

2,4-Dichlorophenoxyacetic Acid 2-Methyl-4-chlorophenoxyacetic Acid

Authors & Affiliations

4 authors, click to expand affiliations / ORCID

Pieper D H

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

Stadler-Fritzsche K

Engesser K H

Knackmuss H J

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Article Info

Journal

Archives of microbiology

Abbr.

Arch Microbiol

ISSN

0302-8933

DOI

10.1007/BF00249121

Published

1993-00-00

Pages

169-78

Language

English

Region

Germany

NLM ID

0410427

Subset

External Links

PubMed source DOI: 10.1007/BF00249121 View journal details

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

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