Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP 134 |
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Authors: | Dietmar Helmut Pieper Karin Stadler-Fritzsche Karl-Heinrich Engesser Hans-Joachim Knackmuss |
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Affiliation: | (1) Abteilung Mikrobiologie, Gesellschaft für Biotechnologische Forschung, Mascheroder Weg 1, D-38124 Braunschweig, Germany;(2) Institut für Mikrobiologie der Universität Stuttgart, Azenbergstrasse 18, D-70174 Stuttgart, Germany |
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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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Keywords: | 2-Chloro-4-methylphenoxyacetic acid 2-Chloro-4-methyl-cis,cis-muconate 4-Carboxymethy 2-chloro-4-methylmuconolactone 4-Carboxychloromethyl-3-methylbut-2-en-4-olide Alcaligenes eutrophus JMP 134 Ortho-cleavage Cycloisomerization |
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