Benzylfumaric, benzylmaleic, and Z- and E-phenylitaconic acids: synthesis, characterization, and correlation with a metabolite generated by Azoarcus tolulyticus Tol-4 during anaerobic toluene degradation.

Applied and Environmental Microbiology
M E MigaudJ W Frost

Abstract

E-Phenylitaconic acid has been isolated as a metabolite generated by Azoarcus tolulyticus Tol-4 along with benzylsuccinic acid during anaerobic degradation of toluene. Strain Tol-4 converted 1 to 2% of toluene carbon to E-phenylitaconate and benzylsuccinate (10:1). The identification of E-phenylitaconic acid was based on 1H nuclear magnetic resonance (NMR) characterization of degradation products derived from 13C-labeled toluene followed by comparison of spectroscopic and chromatographic data for the isolated, unlabeled metabolite with those for chemically synthesized benzylfumaric acid, benzylmaleic acid, E-phenylitaconic acid, and Z-phenylitaconic acid. Spectroscopic comparisons included 1H NMR, 13C NMR, and nuclear overhauser effect correlations. High-pressure liquid chromatography (HPLC) retention times and HPLC coinjections with synthetic dioic acids provided another reliable line of evidence for structure assignment. The formation of E-phenylitaconic acid differs from previous reports of benzylfumaric acid generation along with benzylsuccinic acid during anaerobic microbial degradation of toluene. This has important implications relevant to elaboration of the metabolic route for anaerobic toluene degradation by strain Tol...Continue Reading

References

Sep 1, 1992·Applied and Environmental Microbiology·H R BellerD Grbić-Galić
Sep 1, 1969·The Journal of Applied Bacteriology·J D Owens, R M Keddie
Nov 1, 1994·Applied and Environmental Microbiology·B SeyfriedJ Zeyer
Aug 1, 1994·Applied and Environmental Microbiology·M R FriesJ M Tiedje

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Citations

Feb 1, 1997·European Journal of Biochemistry·J Heider, G Fuchs
Mar 10, 2004·Applied and Environmental Microbiology·Yoshifumi ShinodaNobuo Kato
Oct 4, 2011·Nature Reviews. Microbiology·Georg FuchsJohann Heider
Feb 1, 1997·Journal of Bacteriology·H R Beller, A M Spormann
Feb 1, 1997·Applied and Environmental Microbiology·P W Coschigano, L Y Young

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