5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel “one-carbon removal pathways”

Wang, Ning; Buck, Robert C.; Szostek, Bogdan; Sulecki, Lisa M.; Wolstenholme, Barry W.

doi:10.1016/j.chemosphere.2011.12.056

Cited by 85 publications

(102 citation statements)

References 18 publications

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“…As the accurate mass of fluorine (m/z = 18.998) is very close to its nominal mass, mass-defect filtration (-50 to +10 mDa) of nominal masses could eliminate the majority of irrelevant information in the full-scan MS spectrum [27]. Comparison of differences in full-scan chromatograms of paired live and matrix samples could also help find signals that might represent potential transformation products that existed in live samples only [38]. A limited number of rational molecular compositions by a combination of C, H, F, O, N elements could be further obtained with a mass accuracy of less than 5 ppm [27,39,58].…”

Section: Mass-spectrometry Elucidation Of Novel Transformation Productsmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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A B S T R A C TBiotransformation of polyfluoroalkyl precursors contributes in part to the perfluoroalkyl carboxylates and sulfonates detected in the global environment and biota. Robust sample preparation and sensitive analytical techniques for maximum analyte recovery are essential to identify and to quantify biotransformation products often present at low levels in environmental matrices and experimental systems. This critical review covers current sample-preparation and analytical methods, including extraction, concentration, clean-up and derivatization, mass spectrometry coupled to gas or liquid chromatography, and radioisotope labeling and tracking techniques. We also critically review methodologies for molecular structural elucidation and in-silico prediction of potential transformation products. We describe current knowledge gaps and challenges in studying novel alternative polyfluoroalkyl substances. We discuss future trends on utilizing advanced analytical techniques.

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Section: Mass-spectrometry Elucidation Of Novel Transformation Productsmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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“…Similarly, when 6:2 FTUCA was added to activated sludge, its possible intermediates leading to 5:2 ketone were also not observed by high-resolution mass spectrometry analysis. 38 We are in the process of acquiring 6:2 FTUI standard to be dosed to soil samples to see if it can be converted to PFHpA by soil microbial enzymes via five possible enzymatic steps described in Figure SI (Figure 4), the terminal iodide on 6:2 FTI was first hydrolytically substituted with a hydroxyl group to form 6:2 FTOH, as observed by LC/MS/MS analysis. 6:2 FTOH was rapidly biotransformed to downstream major products, such as PFPeA, PFHxA, and x:3 acids, as also occurred in soil dosed with 6:2 FTOH as the starting material.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Aerobic Soil Biotransformation of 6:2 Fluorotelomer Iodide

Ruan

Szostek

Folsom

et al. 2013

Environ. Sci. Technol.

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6:2 FTI [F(CF 2 ) 6 CH 2 CH 2 I] is a principal industrial raw material used to manufacture 6:2 FTOH [F(CF 2 ) 6 CH 2 CH 2 OH] and 6:2 FTOH-based products and could enter aerobic environments from possible industrial emissions where it is manufactured. This is the first study to assess 6:2 FTI aerobic soil biotransformation, quantify transformation products, and elucidate its biotransformation pathways. 6:2 FTI biotransformation led to 6:2 FTOH as a key intermediate, which was subsequently biotransformed to other significant transformation products, including PFPeA [F-(CF 2 ) 4 COOH, 20 mol % at day 91], 5:3 acid [F-(CF 2 ) 5 CH 2 CH 2 COOH, 16 mol %], PFHxA [F(CF 2 ) 5 COOH, 3.8 mol %], and 4:3 acid [F(CF 2 ) 4 CH 2 CH 2 COOH, 3.0 mol %]. 6:2 FTI biotransformation also led to a significant level of PFHpA [F(CF 2 ) 6 COOH, 16 mol % at day 91], perhaps via another putative intermediate, 6:2 FTUI [F(CF 2 ) 6 CHCHI],whose molecular identity and further biotransformation were not verified because of the lack of an authentic standard. Total recovery of the aforementioned per-and polyfluorocarboxylates accounted for 59 mol % of initially applied 6:2 FTI by day 91, in comparison to 56 mol % when soil was dosed with 6:2 FTOH, which did not lead to PFHpA. Thus, were 6:2 FTI to be released from its manufacture and undergo soil microbial biotransformation, it could form PFPeA, PFHpA, PFHxA, 5:3 acid, and 4:3 acid in the environment.

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“…A number of studies presented the degradability and the fate of PFC precursors, such as fluorotelomer alcohols in sediments resulting in perfluorinated carboxylic acids [43,44]. Nevertheless, no TPs of perfluoroctanoate (PFOA) have been reported, stressing that these compounds are very stable and hardly degradable [59,60].…”

Section: Transformation Products Formed By Microbial Metabolismmentioning

confidence: 99%

“…There are few studies with direct injection of environmental samples for the identification of TPs. More often, sediments, activated sludge, wastewater and river-water samples were collected and subjected to solid-phase extraction (SPE) or liquidliquid extraction (LLE) prior to analysis, for enrichment of the analytes [35,44,51]. To achieve sufficient enrichment for a broad range of compounds, including TPs with different physical-chemical properties, Kern et al used simultaneously four different SPE sorbents in one HPLC-UV, UPLC-Q-ToF-MS/MS Waters MassLynx, mass accuracy, fragmentation pattern [75] cartridge (weak anion, weak cation-exchange material, and nonpolar and hydrophilic-lipophilic interaction sorbents) [5].…”

Section: Identification Approaches -Laboratory Studiesmentioning

confidence: 99%

Targeted and non-targeted liquid chromatography-mass spectrometric workflows for identification of transformation products of emerging pollutants in the aquatic environment

Bletsou

Jeon

Hollender

et al. 2015

TrAC Trends in Analytical Chemistry

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184

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A B S T R A C TIdentification of transformation products (TPs) of emerging pollutants is challenging, due to the vast number of compounds, mostly unknown, the complexity of the matrices and their often low concentrations, requiring highly selective, highly sensitive techniques. We compile background information on biotic and abiotic formation of TPs and analytical developments over the past five years. We present a database of biotic or abiotic TPs compiled from those identified in recent years. We discuss mass spectrometric (MS) techniques and workflows for target, suspect and non-target screening of TPs with emphasis on liquid chromatography coupled to MS (LC-MS). Both low-and high-resolution (HR) mass analyzers have been applied, but HR-MS is the technique of choice, due to its high confirmatory capabilities, derived from the high resolving power and the mass accuracy in MS and MS/MS modes, and the sophisticated software developed.

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5:3 Polyfluorinated acid aerobic biotransformation in activated sludge via novel “one-carbon removal pathways”

Cited by 85 publications

References 18 publications

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Aerobic Soil Biotransformation of 6:2 Fluorotelomer Iodide

Targeted and non-targeted liquid chromatography-mass spectrometric workflows for identification of transformation products of emerging pollutants in the aquatic environment

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