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, Katrin Pollmann, Patricia Nikodem, Bernardo Gonzalez, Victor Wray

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21 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1466-1470
Number of pages5
JournalJournal of Bacteriology
Volume184
Issue number5
DOIs
StatePublished - 2002

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