Evidence for the Formation of Difluoroacetic Acid in Chlorofluorocarbon-Contaminated Ground Water

Dorgerloh, Ute; Becker, Roland; Kaiser, Melanie

doi:10.3390/molecules24061039

Cited by 6 publications

(6 citation statements)

References 24 publications

(27 reference statements)

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“…Trifluoroacetic acid (TFA) is a persistent, highly water soluble industrial chemical, which is also derived by (photo)degradation from refrigerants, (per)fluorinated chemicals, pharmaceuticals, and pesticides [96]. Difluoroacetic acid (DFA) is probably mostly derived from TFA and has not yet been considered in the environment before [97]. Oxamic acid is an oxidation product formed upon ozonation during drinking water treatment, most likely derived from N-containing organic matter [98].…”

Section: Applicability Of the Methods To Other Anionic Contaminantsmentioning

confidence: 99%

Capillary electrophoresis-mass spectrometry for the direct analysis of glyphosate: method development and application to beer beverages and environmental studies

et al. 2020

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In this study, we developed and validated a CE-TOF-MS method for the quantification of glyphosate (N-(phosphonomethyl)glycine) and its major degradation product aminomethylphosphonic acid (AMPA) in different samples including beer, media from toxicological analysis with Daphnia magna, and sorption experiments. Using a background electrolyte (BGE) of very low pH, where glyphosate is still negatively charged but many matrix components become neutral or protonated, a very high separation selectivity was reached. The presence of inorganic salts in the sample was advantageous with regard to preconcentration via transient isotachophoresis. The advantages of our new method are the following: no derivatization is needed, high separation selectivity and thus matrix tolerance, speed of analysis, limits of detection suitable for many applications in food and environmental science, negligible disturbance by metal chelation. LODs for glyphosate were < 5 μg/L for both aqueous and beer samples, the linear range in aqueous samples was 5-3000 μg/L, for beer samples 10-3000 μg/L. For AMPA, LODs were 3.3 and 30.6 μg/L, and the linear range 10-3000 μg/L and 50-3000 μg/L, for aqueous and beer samples, respectively. Recoveries in beer samples for glyphosate were 94.3-110.7% and for AMPA 80.2-100.4%. We analyzed 12 German and 2 Danish beer samples. Quantification of glyphosate and AMPA was possible using isotopically labeled standards without enrichment, purification, or dilution, only degassing and filtration were required for sample preparation. Finally, we demonstrate the applicability of the method for other strong acids, relevant in food and environmental sciences such as N-acetyl glyphosate, Nacetyl AMPA (present in some glyphosate resistant crop), trifluoroacetic acid, 2-methyl-4-chlorophenoxyacetic acid, glufosinate and its degradation product 3-(methylphosphinico)propionic acid, oxamic acid, and others.

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Section: Applicability Of the Methods To Other Anionic Contaminantsmentioning

confidence: 99%

Capillary electrophoresis-mass spectrometry for the direct analysis of glyphosate: method development and application to beer beverages and environmental studies

et al. 2020

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“…Incidentally, CFCs have also been found in groundwater samples, even in 2019, and have been shown to degrade to the toxic compound difluoroacetic acid. 232 …”

Section: Metabolism Of Fluorine-containing Drugsmentioning

confidence: 99%

“…In fact, CFCs have been largely replaced with hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs) which do not have such a disastrous effect on the ozone layer; given their shorter half-life, they mainly remain within the lower atmosphere and generally do not reach the stratosphere (Scheme ). Incidentally, CFCs have also been found in groundwater samples, even in 2019, and have been shown to degrade to the toxic compound difluoroacetic acid …”

Section: Metabolism Of Fluorine-containing Drugsmentioning

confidence: 99%

“…Incidentally, CFCs have also been found in groundwater samples, even in 2019, and have been shown to degrade to the toxic compound difluoroacetic acid. 232 Nevertheless, the newer HFCs are also beginning to be more restricted in their use in recent years. Although they do not contribute as much to the depletion of the ozone layer, they are in fact greenhouse gases and contribute significantly to global warming through the absorption of IR radiation.…”

Section: Environmental Factors and Bioaccumulation Of Fluorine-contai...mentioning

confidence: 99%

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Chemical Aspects of Human and Environmental Overload with Fluorine

et al. 2021

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Over the last 100–120 years, due to the ever-increasing importance of fluorine-containing compounds in modern technology and daily life, the explosive development of the fluorochemical industry led to an enormous increase of emission of fluoride ions into the biosphere. This made it more and more important to understand the biological activities, metabolism, degradation, and possible environmental hazards of such substances. This comprehensive and critical review focuses on the effects of fluoride ions and organofluorine compounds (mainly pharmaceuticals and agrochemicals) on human health and the environment. To give a better overview, various connected topics are also discussed: reasons and trends of the advance of fluorine-containing pharmaceuticals and agrochemicals, metabolism of fluorinated drugs, withdrawn fluorinated drugs, natural sources of organic and inorganic fluorine compounds in the environment (including the biosphere), sources of fluoride intake, and finally biomarkers of fluoride exposure.

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“…Difluoroacetate is a transformation product of various xenobiotics including the refrigerant chlorotrifluoroethylene (R1113) 46 and the anesthetic 1,1,2,2-tetrafluoro-1-(2,2,2trifluoroethoxy)-ethane 47 . It is a byproduct of the photodegradation of penoxsulam, a widely used pesticide 48 .…”

Section: Chimeric Defluorinases Indicate Importance Of the C-terminal...mentioning

confidence: 99%

Enzymatic carbon-fluorine bond cleavage by human gut microbes

Probst,

Felder,

Poltorak

et al. 2024

Preprint

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The human gut microbiota is known for its pharmaceutical biotransformation capabilities. Many pharmaceuticals are fluorinated; however, it was previously unknown whether gut microbes were capable of cleaving carbon-fluorine bonds. Here we show that dehalogenases encoded by human gut microbes, including Clostridia, Bacilli, and Coriobacteriia, are active on fluorinated amino and organic acids. Through the development of a rapid, 96-well fluoride detection assay, we screened and characterized new microbial gut defluorinases. Using alanine scanning and chimeric protein design, we identified a 41 amino acid carboxyl-terminal region which is necessary and sufficient to enable defluorination activity when fused to a non-defluorinating dehalogenase. Based on this carboxyl-terminal region alone, we were able to predict the defluorination or non-defluorination activity of microbial dehalogenases with >83% accuracy. By uncovering the hidden potential of human gut microbes to catalyze defluorination reactions, our findings lay the foundation for therapeutic interventions relevant to human and gut microbiome health.

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Evidence for the Formation of Difluoroacetic Acid in Chlorofluorocarbon-Contaminated Ground Water

Cited by 6 publications

References 24 publications

Capillary electrophoresis-mass spectrometry for the direct analysis of glyphosate: method development and application to beer beverages and environmental studies

Capillary electrophoresis-mass spectrometry for the direct analysis of glyphosate: method development and application to beer beverages and environmental studies

Chemical Aspects of Human and Environmental Overload with Fluorine

Enzymatic carbon-fluorine bond cleavage by human gut microbes

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