Skip to main content
  • ASM
    • Antimicrobial Agents and Chemotherapy
    • Applied and Environmental Microbiology
    • Clinical Microbiology Reviews
    • Clinical and Vaccine Immunology
    • EcoSal Plus
    • Eukaryotic Cell
    • Infection and Immunity
    • Journal of Bacteriology
    • Journal of Clinical Microbiology
    • Journal of Microbiology & Biology Education
    • Journal of Virology
    • mBio
    • Microbiology and Molecular Biology Reviews
    • Microbiology Resource Announcements
    • Microbiology Spectrum
    • Molecular and Cellular Biology
    • mSphere
    • mSystems
  • Log in
  • My alerts
  • My Cart

Main menu

  • Home
  • Articles
    • Current Issue
    • Accepted Manuscripts
    • COVID-19 Special Collection
    • Archive
    • Minireviews
  • For Authors
    • Submit a Manuscript
    • Scope
    • Editorial Policy
    • Submission, Review, & Publication Processes
    • Organization and Format
    • Errata, Author Corrections, Retractions
    • Illustrations and Tables
    • Nomenclature
    • Abbreviations and Conventions
    • Publication Fees
    • Ethics Resources and Policies
  • About the Journal
    • About AEM
    • Editor in Chief
    • Editorial Board
    • For Reviewers
    • For the Media
    • For Librarians
    • For Advertisers
    • Alerts
    • RSS
    • FAQ
  • Subscribe
    • Members
    • Institutions
  • ASM
    • Antimicrobial Agents and Chemotherapy
    • Applied and Environmental Microbiology
    • Clinical Microbiology Reviews
    • Clinical and Vaccine Immunology
    • EcoSal Plus
    • Eukaryotic Cell
    • Infection and Immunity
    • Journal of Bacteriology
    • Journal of Clinical Microbiology
    • Journal of Microbiology & Biology Education
    • Journal of Virology
    • mBio
    • Microbiology and Molecular Biology Reviews
    • Microbiology Resource Announcements
    • Microbiology Spectrum
    • Molecular and Cellular Biology
    • mSphere
    • mSystems

User menu

  • Log in
  • My alerts
  • My Cart

Search

  • Advanced search
Applied and Environmental Microbiology
publisher-logosite-logo

Advanced Search

  • Home
  • Articles
    • Current Issue
    • Accepted Manuscripts
    • COVID-19 Special Collection
    • Archive
    • Minireviews
  • For Authors
    • Submit a Manuscript
    • Scope
    • Editorial Policy
    • Submission, Review, & Publication Processes
    • Organization and Format
    • Errata, Author Corrections, Retractions
    • Illustrations and Tables
    • Nomenclature
    • Abbreviations and Conventions
    • Publication Fees
    • Ethics Resources and Policies
  • About the Journal
    • About AEM
    • Editor in Chief
    • Editorial Board
    • For Reviewers
    • For the Media
    • For Librarians
    • For Advertisers
    • Alerts
    • RSS
    • FAQ
  • Subscribe
    • Members
    • Institutions
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
Christian Behrend
Institut für Biochemie, Universität Witten/Herdecke, D-58453 Witten, Germany
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Kerstin Heesche-Wagner
Institut für Biochemie, Universität Witten/Herdecke, D-58453 Witten, Germany
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
DOI: 10.1128/AEM.65.4.1372-1377.1999
  • Article
  • Figures & Data
  • Info & Metrics
  • PDF
Loading

Article Figures & Data

Figures

  • Tables
  • Fig. 1.
    • Open in new tab
    • Download powerpoint
    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.
    • Open in new tab
    • Download powerpoint
    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
    • Open in new tab
    • Download powerpoint
  • Fig. 3.
    • Open in new tab
    • Download powerpoint
    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.
    • Open in new tab
    • Download powerpoint
    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.
    • Open in new tab
    • Download powerpoint
    Fig. 5.

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

  • Fig. 6.
    • Open in new tab
    • Download powerpoint
    Fig. 6.

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

Tables

  • Figures
  • 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 )e3.34 ppm (s)3.57 ppm (s)
    H57.50 ppm (d )f7.33 ppm (d)7.42 ppm (dd)7.39 ppm (d)
    H65.90 ppm (d)5.08 ppm (d)6.45 ppm (d)5.16 ppm (d)
    3J(H5H6) = 10.2 Hz3J(H5H6) = 9.2 Hz3J(H5H6) = 10.5 Hz3J(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.

PreviousNext
Back to top
Download PDF
Citation Tools
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
Applied and Environmental Microbiology Apr 1999, 65 (4) 1372-1377; DOI: 10.1128/AEM.65.4.1372-1377.1999

Citation Manager Formats

  • BibTeX
  • Bookends
  • EasyBib
  • EndNote (tagged)
  • EndNote 8 (xml)
  • Medlars
  • Mendeley
  • Papers
  • RefWorks Tagged
  • Ref Manager
  • RIS
  • Zotero
Print

Alerts
Sign In to Email Alerts with your Email Address
Email

Thank you for sharing this Applied and Environmental Microbiology article.

NOTE: We request your email address only to inform the recipient that it was you who recommended this article, and that it is not junk mail. We do not retain these email addresses.

Enter multiple addresses on separate lines or separate them with commas.
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
(Your Name) has forwarded a page to you from Applied and Environmental Microbiology
(Your Name) thought you would be interested in this article in Applied and Environmental Microbiology.
CAPTCHA
This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Share
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
Applied and Environmental Microbiology Apr 1999, 65 (4) 1372-1377; DOI: 10.1128/AEM.65.4.1372-1377.1999
del.icio.us logo Digg logo Reddit logo Twitter logo CiteULike logo Facebook logo Google logo Mendeley logo
  • Top
  • Article
    • ABSTRACT
    • MATERIALS AND METHODS
    • RESULTS
    • DISCUSSION
    • ACKNOWLEDGMENTS
    • FOOTNOTES
    • REFERENCES
  • Figures & Data
  • Info & Metrics
  • PDF

Related Articles

Cited By...

About

  • About AEM
  • Editor in Chief
  • Editorial Board
  • Policies
  • For Reviewers
  • For the Media
  • For Librarians
  • For Advertisers
  • Alerts
  • RSS
  • FAQ
  • Permissions
  • Journal Announcements

Authors

  • ASM Author Center
  • Submit a Manuscript
  • Article Types
  • Ethics
  • Contact Us

Follow #AppEnvMicro

@ASMicrobiology

       

ASM Journals

ASM journals are the most prominent publications in the field, delivering up-to-date and authoritative coverage of both basic and clinical microbiology.

About ASM | Contact Us | Press Room

 

ASM is a member of

Scientific Society Publisher Alliance

 

American Society for Microbiology
1752 N St. NW
Washington, DC 20036
Phone: (202) 737-3600

Copyright © 2021 American Society for Microbiology | Privacy Policy | Website feedback

 

Print ISSN: 0099-2240; Online ISSN: 1098-5336