Conversion of 2-chloromaleylacetate in Alcaligenes eutrophus JMP134
Related Experiment Video
Updated: Nov 7, 2026
A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
Published on: October 2, 2012
M D Vollmer1, K Stadler-Fritzsche, M Schlömann
1Institut für Mikrobiologie, Universität Stuttgart, Federal Republic of Germany.
Abstract:
2,4-Dichlorophenoxyacetate (2,4-D) in Alcaligenes eutrophus JMP134 (pJP4) is degraded via 2-chloromaleylacetate as an intermediate. The latter compound was found to be reduced by NADH in a maleylacetate reductase catalyzed reaction. Maleylacetate and chloride were formed as products of 2-chloromaleylacetate reduction, the former being funneled into the 3-oxoadipate pathway by a second reductive step. There was no indication for an involvement of a pJP4-encoded enzyme in either the reduction or the dechlorination reaction.
Related Concept Videos
00:51Base-Promoted α-Halogenation of Aldehydes and Ketones
01:21Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...