Synthesis of reference substances for highly polar metabolites of nitroaromatic compounds

Schmidt, Torsten; Steinbach, K; Buetehorn, Ulf; Heck, K.; Volkwein, U.; Stork, G.

doi:10.1016/s0045-6535(98)00518-9

Cited by 11 publications

(14 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To our knowledge, this is the first report of the aminomethylnitrocatechol isomers. 2-Amino-4,6-dinitrobenzyl alcohol and 4-amino-2,4-dinitrobenzyl alcohol have been chemically synthesized (27). Mass spectra of the underivatized 2-amino-4,6-dinitrobenzyl alcohol ([M] ϩ 213, 196, 179) from our reactions (not shown) correspond with the major ion fragments reported by Schmidt et al (27).…”

Section: Transformation Of Adntsupporting

confidence: 72%

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Johnson¹,

Smets

Spain³

2001

Appl Environ Microbiol

View full text Add to dashboard Cite

The electron-withdrawing nitro substituents of 2,4,6-trinitrotoluene (TNT) make the aromatic ring highly resistant to oxidative transformation. The typical biological transformation of TNT involves reduction of one or more of the nitro groups of the ring to produce the corresponding amine. Reduction of a single nitro substituent of TNT to an amino substituent increases the electron density of the aromatic nucleus considerably. The comparatively electron-dense nuclei of the aminodinitrotoluene (ADNT) isomers would be expected to be more susceptible to oxygenase attack than TNT. The hypothesis was tested by evaluating three nitroarene dioxygenases for the ability to hydroxylate the ADNT isomers. The predominant reaction was dioxygenation of the ring to yield nitrite and the corresponding aminomethylnitrocatechol. A secondary reaction was benzylic monooxygenation to form aminodinitrobenzyl alcohol. The substrate preferences and catalytic specificities of the three enzymes differed considerably. The discovery that the ADNT isomers are substrates for the nitroarene dioxygenases reveals the potential for extensive bacterial transformation of TNT under aerobic conditions.

show abstract

Section: Transformation Of Adntsupporting

confidence: 72%

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Johnson¹,

Smets

Spain³

2001

Appl Environ Microbiol

View full text Add to dashboard Cite

show abstract

“…1), and 15 N 2 -labeled 2,4-dinitrotoluene-3-sulfonic acid were synthesized, purified, and characterized by Dr. Klaus Steinbach, Department of Chemistry, PhilippsUniversity of Germany [21,22]. Stock solutions (1 µg µL -1 ) of 2-amino-4-nitrotoluene-5-sulfonic acid (2A4NTSA-5), 4-amino-2-nitrotoluene-3-sulfonic acid (4A2NTSA-3), 2,4-dinitrotoluene-3-sulfonic acid (2,4DNTSA-3), 2,4-dinitrotoluene-5-sulfonic acid (2,4DNTSA-5), 2,6-dinitrotoluene-3-sulfonic acid (2,6DNTSA-3), and 2,6-dinitrotoluene-4-sulfonic acid (2,6DNTSA-4), and 6.4 ng µL -1 of 15 N 2 -labeled 2,4-dinitrotoluene-3-sulfonic acid were prepared in methanol.…”

Section: Methodsmentioning

confidence: 99%

“…Sulfonic acid-substituted nitrotoluenes were recently detected in soil near a former ammunition plant located in Stadtallendorf, Germany [22]. Dinitro-toluenesulfonic acids were produced during the manufacture of 2,4,6-TNT when sodium sulfite (Na 2 SO 3 ) was used to remove unwanted asymmetric TNT by-products.…”

Section: Introductionmentioning

confidence: 99%

“…Dinitro-toluenesulfonic acids were produced during the manufacture of 2,4,6-TNT when sodium sulfite (Na 2 SO 3 ) was used to remove unwanted asymmetric TNT by-products. It has been found that one nitro group in the dinitro-toluenesulfonic acids might easily be reduced into amino group to form aminonitro-toluenesulfonic acids under different environmental conditions [22]. Because dinitro-toluenesulfonic acids and amino-nitro-toluenesulfonic acids are extremely polar and highly soluble in water [1,22], their contamination of environmental water might be more likely than of soil.…”

Section: Introductionmentioning

confidence: 99%

“…Quantitative analysis of dinitro-and amino-nitro-toluenesulfonic acids in water has, however, been a big challenge not only because of to their high hydrophilicity but also because authentic standards are not commercially available [22]. Traditional GC or GC-MS is not amendable to direct analysis of these compounds because of their high polarity.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Analysis of dinitro- and amino-nitro-toluenesulfonic acids in groundwater by solid-phase extraction and liquid chromatography?mass spectrometry

Tang

Steinbach

Cai

2004

Analytical and Bioanalytical Chemistry

Self Cite

View full text Add to dashboard Cite

A reversed-phase LC-MS method with quadrupole-time of flight (QTOF) detection has been developed for the determination of four dinitro-toluenesulfonic acids and two amino-nitro-toluenesulfonic acids in groundwater. The analytes were separated by HPLC with 0.1% ( v/ v) formic acid as mobile phase modifier compatible with mass spectrometric detection. QTOF-MS analysis with negative ion electrospray ionization afforded good selectivity and sensitivity for analysis of the dinitro- and amino-nitro-toluenesulfonic acids. Structure elucidation and confirmation were accomplished by tandem mass spectrometry. Characteristic ions resulting from the loss of NO, NO(2), and SO(2) from the [M-H](-) ions were detected. An intense fragment ion at m/ z 80 representing the [SO(3)](-) ion was detected for all dinitro- and amino-nitro-toluenesulfonic acids. Solid-phase extraction using a co-polymer cartridge was developed for preconcentration of the analytes from water. Good recovery (>85%) was achieved when 0.1% formic acid was added into the water samples before extraction. Method detection limits ranged from 10 to 76 ng L(-1) for the targeted compounds when 10 mL water was analyzed. Groundwater samples collected from wells close to a former ammunition plant in Stadtallendorf, Germany, were analyzed for the dinitro- and amino-nitro-toluenesulfonic acids.

show abstract

Use of the Spectrometric Sum Parameter for Aromatic Amines in the Monitoring of a Former Ammunition Plant

Schmidt¹,

Bütehorn

Steinbach

et al. 2000

Acta hydrochim. hydrobiol.

View full text Add to dashboard Cite

Synthesis of reference substances for highly polar metabolites of nitroaromatic compounds

Cited by 11 publications

References 12 publications

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Analysis of dinitro- and amino-nitro-toluenesulfonic acids in groundwater by solid-phase extraction and liquid chromatography?mass spectrometry

Use of the Spectrometric Sum Parameter for Aromatic Amines in the Monitoring of a Former Ammunition Plant

Contact Info

Product

Resources

About