Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP 134.
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.
Pieper
D H
DH
Abteilung Mikrobiologie, Gesellschaft für Biotechnologische Forschung, Braunschweig, Germany.
Stadler-Fritzsche
K
K
Engesser
K H
KH
Knackmuss
H J
HJ
D015084:2,4-Dichlorophenoxyacetic Acid / Q000378:metabolism; D008456:2-Methyl-4-chlorophenoxyacetic Acid / Q000737:chemistry / Q000378:metabolism*; D000421:Alcaligenes / Q000378:metabolism*; D001673:Biodegradation, Environmental; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D015084:2,4-Dichlorophenoxyacetic Acid; D008456:2-Methyl-4-chlorophenoxyacetic Acid