Metabolites from fungal laccase-catalysed transformation of sulfonamides |
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| Institution: | 1. University of Rostock, Institute of Land Use, Justus-von-Liebig Weg 6, D-18059 Rostock, Germany;2. Institute of Organic and Environmental Chemistry, University of Koblenz-Landau, D-76829 Landau, Germany;3. University of Trier, Soil Science, Behringstrasse 21, D-54286 Trier, Germany;1. School of Architecture, Civil and Environmental Engineering (ENAC), Ecole Polytechnique Fédérale de Lausanne (EPFL), Station 2, 1015 Lausanne, Switzerland;2. Faculty of Geosciences and the Environment, University of Lausanne, 1015 Lausanne, Switzerland;3. Eawag, Swiss Federal Institute of Aquatic Science and Technology, Überlandstrasse 133, 8600 Dübendorf, Switzerland;1. Université de Montpellier 2, Institut Européen des Membranes, UMR 5635 (CNRS-ENSCM-UM2), CC 047, 2 Place Eugène Bataillon, 34095 Montpellier Cedex 5, France;2. Catalan Institute for Water Research (ICRA), Scientific and Technological Park of the University of Girona, H2O building, C/Emili Grahit 101, E-17003 Girona, Spain;3. Da Volterra, Le Dorian, building B1, 172 rue de Charonne, 75011 Paris, France;4. Water and Soil Quality Research Group, Dept. of Environmental Chemistry, IDAEA-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain;1. Fujian Key Laboratory of Marine Enzyme Engineering, Fuzhou University, Fujian 350116, China;2. Technical Center, Fujian Entry-Exit Inspection and Quarantine Bureau, Fuzhou, Fujian 350001, China;3. School of Biomedical Sciences, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China;1. Strategic Water Infrastructure Laboratory, School of Civil, Mining and Environmental Engineering, University of Wollongong (UOW), NSW 2522, Australia;2. Wollongong Isotope Geochronology Laboratory, School of Earth and Environmental Sciences, UOW, NSW 2522, Australia;3. School of Chemistry, UOW, NSW 2522, Australia;4. Strategic Water Infrastructure Laboratory, School of Chemistry, UOW, NSW 2522, Australia;1. Department of Environmental Health Engineering, School of Public Health, Iran University of Medical Sciences, Tehran, Iran;2. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, P.O. Box 14155–6451, Tehran 14176, Iran;3. Department of Environmental Health Engineering, School of Public Health, Center for Solid Waste Research, Institute of Public Health Research, Tehran University of Medical Sciences, Tehran, Iran;4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran |
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| Abstract: | Soil metabolism of sulfonamides is largely unknown. Hence the sulfonamides sulfanilamide (SAA), sulfadimethoxine (SDT) and sulfapyridine (SPY) were reacted in model experiments with a fungal laccase from Trametes versicolor. Enzymatic transformation after a reaction time of 15 d ranged from 10.0% for SAA up to 95.6% for SPY and the difference was attributed to the different molecular substituents. Metabolites were first tentatively assigned after LC–ESI+–MS full-scan analysis. Secondly, the proposed metabolites were further confirmed employing either multiple reaction monitoring in comparison with standard substances or precursor ion scan LC–ESI+–MS/MS experiments striving for the precursor and two to three product ions. Aniline was confirmed as a breakdown product of SPY and further metabolites of SPY and of SDT were identified as rearranged SO2 extrusion products. Thirdly, some of the metabolites matched those that were previously reported for sulfonamide photodegradation and degradation in soil. It was concluded that enzymatic metabolism as investigated here also occurs in soil. |
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