ENVIRONMENTAL AND PUBLIC HEALTH MICROBIOLOGY

Formation of Hydride-Meisenheimer Complexes of Picric Acid (2,4,6-Trinitrophenol) and 2,4-Dinitrophenol during Mineralization of Picric Acid by Nocardioides sp. Strain CB 22-2

Christian Behrend, Kerstin Heesche-Wagner
DOI: 

Article Figures & Data

Figures

  • Fig. 1.
    Fig. 1.

    [H−]-Meisenheimer complex formation during conversion of picric acid by cell extracts ofNocardioides sp. strain CB 22-2. UV spectra were recorded at zero time (——), 5 min (––––), 15 min (····), and 25 min (–··–).

  • Fig. 2.
    Fig. 2.

    Degradation of the [H−]-Meisenheimer complex of picric acid by cell extracts of Nocardioides sp. strain CB 22-2 with formation of 2,4-DNP. UV spectra were recorded at zero time (——), 2 min (––––), 4 min (····), and 8 min (–··–).

  • Figure3
  • Fig. 3.
    Fig. 3.

    Formation of the [H−]-Meisenheimer complex of 2,4-DNP during conversion of 2,4-DNP by cell extracts ofNocardioides sp. strain CB 22-2. UV spectra were recorded at zero time (——), 4 min (––––), and 12 min (····).

  • Fig. 4.
    Fig. 4.

    UV-visible light spectra after HPLC analysis for a retention time of 2.07 min, showing the curves for the Meisenheimer complex of 2,4-DNP. The dashed line is the curve for the synthetic complex, and the solid line is the curve for the culture supernatant.

  • Fig. 5.
    Fig. 5.

    First three steps in picric acid metabolism byNocardioides sp. strain CB 22-2.

  • Fig. 6.
    Fig. 6.

    Hypothetical mechanism for NADPH-dependent conversion of H−-DNP.

Tables

  • Table 1.

    Growth and picric acid degradation rates ofNocardioides sp. strain CB 22-2

    Mineral salts mediumGrowth conditionsGrowth rate (h−1)Degradation rate (μmol/h/g [dry wt] of cells)Yield (g [dry wt] of cells/g of picric acid)Amt of nitrite released (mol/mol of picric acid)
    AFlask0.058 ± 0.0039200.27 ± 0.022.9 ± 0.1
    AFermentor0.087 ± 0.0011,6000.29 ± 0.022.9 ± 0.1
    BFlask0.035 ± 0.0028500.19 ± 0.022.2 ± 0.2
  • Table 2.

    1H NMR chemical shift and coupling constants for H−-DNP, 1,5-dinitro-3-methyl-3-aza-bicyclo[3.3.1]-nonene-(6)-one-(8) (a derivative of H−-DNP) (compound 1), and 3-[H−]-2,4-dinitroaniline (compound 2)  

    PositionH−-DNP in D2OaH−-DNP in DMSO-d6a,bCompound 1 in CDCl3cCompound 2 in DMSO-d6b,d
    H3, H3′ 3.84 ppm (s )e 3.34 ppm (s)3.57 ppm (s)
    H5 7.50 ppm (d )f 7.33 ppm (d)7.42 ppm (dd)7.39 ppm (d)
    H6 5.90 ppm (d)5.08 ppm (d)6.45 ppm (d)5.16 ppm (d)
    3J(H5H6) = 10.2 Hz 3J(H5H6) = 9.2 Hz 3J(H5H6) = 10.5 Hz 3J(H5H6) = 10 Hzg

    • ↵a Data from this study.

    • b DMSO-d6, dimethyl sulfoxide d6.

    • ↵c Data from reference 24.

    • d Data from reference 7.

    • ↵e s, singlet.

    • ↵f d, doublet.

    • ↵g The value was estimated from the graph.

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