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Journal of Bacteriology, March 2002, p. 1466-1470, Vol. 184, No. 5
0021-9193/02/$04.00+0     DOI: 10.1128/JB.184.5.1466-1470.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.

Monitoring Key Reactions in Degradation of Chloroaromatics by In Situ 1H Nuclear Magnetic Resonance: Solution Structures of Metabolites Formed from cis-Dienelactone

*** Dietmar H. Pieper,1* Katrin Pollmann,1 Patricia Nikodem,1 Bernardo Gonzalez,2 and Victor Wray3

Division of Microbiology,1 Department of Structure Research, GBF—German Research Center for Biotechnology, Braunschweig, Germany,3 Facultad de Ciencias Biológicas, Departamento de Genética Molecular y Microbiologia, Pontificia Universidad Católica de Chile, Santiago, Chile2

Received 1 October 2001/ Accepted 30 November 2001

A 1H nuclear magnetic resonance (1H NMR) assay was used to study the enzymatic transformation of cis-dienelactone, a central intermediate in the degradation of chloroaromatics. It was shown that the product of the cis-dienelactone hydrolase reaction is maleylacetate, in which there is no evidence for the formation of 3-hydroxymuconate. Under acidic conditions, the product structure was 4-carboxymethyl-4-hydroxybut-2-en-4-olide. Maleylacetate was transformed by maleylacetate reductase into 3-oxoadipate, a reaction competing with spontaneous decarboxylation into cis-acetylacrylate. One-dimensional 1H NMR in 1H2O could thus be shown to be an excellent noninvasive tool for monitoring enzyme activities and assessing the solution structure of substrates and products.

* Corresponding author. Mailing address: Bereich Mikrobiologie, AG Biodegradation, Gesellschaft für Biotechnologische Forschung mbH, Mascheroder Weg 1, D-38124 Braunschweig, Germany. Phone: 49/(0)531/6181-467. Fax: 49/(0)531/6181-411. E-mail: dpi{at}gbf.de.

Journal of Bacteriology, March 2002, p. 1466-1470, Vol. 184, No. 5
0021-9193/02/$04.00+0     DOI: 10.1128/JB.184.5.1466-1470.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.



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