title: Systematic Exploration of Biotransformation Reactions of Amine-Containing Micropollutants in Activated Sludge.
abstract: The main removal process for polar organic micropollutants during activated sludge treatment is biotransformation, which often leads to the formation of stable transformation products (TPs). Because the analysis of TPs is challenging, the use of pathway prediction systems can help by generating a list of suspected TPs. To complete and refine pathway prediction, comprehensive biotransformation studies for compounds exhibiting pertinent functional groups under environmentally relevant conditions are needed. Because many polar organic micropollutants present in wastewater contain one or several amine functional groups, we systematically explored amine biotransformation by conducting experiments with 19 compounds that contained 25 structurally diverse primary, secondary, and tertiary amine moieties. The identification of 144 TP candidates and the structure elucidation of 101 of these resulted in a comprehensive view on initial amine biotransformation reactions. The reactions with the highest relevance were N-oxidation, N-dealkylation, N-acetylation, and N-succinylation. Whereas many of the observed reactions were similar to those known for the mammalian metabolism of amine-containing xenobiotics, some N-acylation reactions were not previously described. In general, different reactions at the amine functional group occurred in parallel. Finally, recommendations on how these findings can be implemented to improve microbial pathway prediction of amine-containing micropollutants are given.
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.|Department of Environmental Systems Science (D-USYS), ETH Zürich , 8092 Zürich, Switzerland.
authors: Rebekka
authors: R
authors: Gulde
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.
authors: Ulf
authors: U
authors: Meier
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.
authors: Emma L
authors: EL
authors: Schymanski
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.|Department of Environmental Systems Science (D-USYS), ETH Zürich , 8092 Zürich, Switzerland.
authors: Hans-Peter E
authors: HP
authors: Kohler
authors: School of Civil and Environmental Engineering, Cornell University , Ithaca, New York 14853, United States.
authors: Damian E
authors: DE
authors: Helbling
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.
authors: Samuel
authors: S
authors: Derrer
authors: EMPA, Swiss Federal Laboratories for Materials Science and Technology , 8600 Dübendorf, Switzerland.
authors: Daniel
authors: D
authors: Rentsch
authors: Eawag, Swiss Federal Institute of Aquatic Science and Technology , 8600 Dübendorf, Switzerland.|Department of Environmental Systems Science (D-USYS), ETH Zürich , 8092 Zürich, Switzerland.
authors: Kathrin
authors: K
authors: Fenner
mesh_terms: D000588:Amines / Q000737:chemistry*; D001673:Biodegradation, Environmental; D012722:Sewage / Q000737:chemistry*; D062065:Wastewater / Q000737:chemistry*; D014874:Water Pollutants, Chemical / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000588:Amines; D012722:Sewage; D062065:Wastewater; D014874:Water Pollutants, Chemical