{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,17]],"date-time":"2026-03-17T02:49:33Z","timestamp":1773715773844,"version":"3.50.1"},"reference-count":145,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2017,10,3]],"date-time":"2017-10-03T00:00:00Z","timestamp":1506988800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>In recent decades, the presence of micropollutants in the environment has been extensively studied due to their high frequency of occurrence, persistence and possible adverse effects to exposed organisms. Concerning chiral micropollutants in the environment, enantiomers are frequently ignored and enantiomeric composition often neglected. However, enantioselective toxicity is well recognized, highlighting the need to include enantioselectivity in environmental risk assessment. Additionally, the information about enantiomeric fraction (EF) is crucial since it gives insights about: (i) environmental fate (i.e., occurrence, distribution, removal processes and (bio)degradation); (ii) illicit discharges; (iii) consumption pattern (e.g., illicit drugs, pharmaceuticals used as recreational drugs, illicit use of pesticides); and (iv) enantioselective toxicological effects. Thus, the purpose of this paper is to provide a comprehensive review about the enantioselective occurrence of chiral bioactive compounds in aquatic environmental matrices. These include pharmaceuticals, illicit drugs, pesticides, polychlorinated biphenyls (PCBs) and polycyclic musks (PCMs). Most frequently analytical methods used for separation of enantiomers were liquid chromatography and gas chromatography methodologies using both indirect (enantiomerically pure derivatizing reagents) and direct methods (chiral stationary phases). The occurrence of these chiral micropollutants in the environment is reviewed and future challenges are outlined.<\/jats:p>","DOI":"10.3390\/sym9100215","type":"journal-article","created":{"date-parts":[[2017,10,3]],"date-time":"2017-10-03T11:33:30Z","timestamp":1507030410000},"page":"215","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":37,"title":["Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review"],"prefix":"10.3390","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7245-4552","authenticated-orcid":false,"given":"Cl\u00e1udia","family":"Ribeiro","sequence":"first","affiliation":[{"name":"CESPU, Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal"},{"name":"Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental (CIIMAR\/CIMAR), Universidade do Porto, Rua dos Bragas 289, 4050-123 Porto, Portugal"}]},{"given":"Ana","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Laboratory of Separation and Reaction Engineering\u2014Laboratory of Catalysis and Materials (LSRE-LCM), Faculdade de Engenharia, Universidade do Porto, Rua Dr. Roberto Frias s\/n, 4200-465 Porto, Portugal"}]},{"given":"Alexandra","family":"Maia","sequence":"additional","affiliation":[{"name":"CESPU, Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal"},{"name":"Universidade Cat\u00f3lica Portuguesa, CBQF\u2014Centro de Biotecnologia e Qu\u00edmica Fina\u2014Laborat\u00f3rio Associado, Escola Superior de Biotecnologia, Rua Arquiteto Lob\u00e3o Vital, Apartado 2511, 4202-401 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3320-730X","authenticated-orcid":false,"given":"Maria","family":"Tiritan","sequence":"additional","affiliation":[{"name":"CESPU, Instituto de Investiga\u00e7\u00e3o e Forma\u00e7\u00e3o Avan\u00e7ada em Ci\u00eancias e Tecnologias da Sa\u00fade, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal"},{"name":"Centro Interdisciplinar de Investiga\u00e7\u00e3o Marinha e Ambiental (CIIMAR\/CIMAR), Universidade do Porto, Rua dos Bragas 289, 4050-123 Porto, Portugal"},{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia da Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,10,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3462","DOI":"10.1016\/j.envpol.2010.08.009","article-title":"Prioritizing research for trace pollutants and emerging contaminants in the freshwater environment","volume":"158","author":"Murray","year":"2010","journal-title":"Environ. Pollut."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1016\/j.scitotenv.2016.12.007","article-title":"Persistent organic pollutants in China\u2019s surface water systems","volume":"580","author":"Han","year":"2017","journal-title":"Sci. Total Environ."},{"key":"ref_3","first-page":"1","article-title":"Priority substances and emerging organic pollutants in portuguese aquatic environment: A Review","volume":"238","author":"Ribeiro","year":"2015","journal-title":"Rev. Environ. Contam. Toxicol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/j.watres.2016.02.047","article-title":"Occurrence and removal of organic micropollutants: An overview of the watch list of EU decision 2015\/495","volume":"94","author":"Barbosa","year":"2016","journal-title":"Water Res."},{"key":"ref_5","first-page":"3","article-title":"Environmental fate of chiral pharmaceuticals: Determination, degradation and toxicity","volume":"Volume 2","author":"Lichtfouse","year":"2012","journal-title":"Environmental Chemistry for a Sustainable World"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.jhazmat.2017.05.015","article-title":"Risk assessment of the endocrine-disrupting effects of nine chiral pesticides","volume":"338","author":"Song","year":"2017","journal-title":"J. Hazard. Mater."},{"key":"ref_7","unstructured":"Albuquerque, N.C.P., Carr\u00e3o, D.B., Habenschus, M.D., and Oliveira, A.R.M. (2017). Metabolism studies of chiral pesticides: A critical review. J. Pharm. Biomed. Anal., in press."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2371","DOI":"10.1016\/j.envpol.2010.03.014","article-title":"Enantioselectivity in environmental risk assessment of modern chiral pesticides","volume":"158","author":"Ye","year":"2010","journal-title":"Environ. Pollut."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3197","DOI":"10.1016\/S0043-1354(01)00026-4","article-title":"Selective degradation of ibuprofen and clofibric acid in two model river biofilm systems","volume":"35","author":"Winkler","year":"2001","journal-title":"Water Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1021\/es0012570","article-title":"Enantiomeric composition of chiral polychlorinated biphenyl atropisomers in aquatic bed sediment","volume":"35","author":"Wong","year":"2001","journal-title":"Environ. Sci. Technol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1002\/chir.21023","article-title":"Enantioselective degradation of warfarin in soils","volume":"24","author":"Lao","year":"2012","journal-title":"Chirality"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1016\/j.scitotenv.2006.09.023","article-title":"Concentrations, enantiomeric compositions, and sources of HCH, DDT and chlordane in soils from the Pearl River Delta, South China","volume":"372","author":"Li","year":"2006","journal-title":"Sci. Total Environ."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"5708","DOI":"10.1016\/j.watres.2013.06.057","article-title":"Stereoselective biodegradation of amphetamine and methamphetamine in river microcosms","volume":"47","author":"Bagnall","year":"2013","journal-title":"Water Res."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Maia, A.S., Ribeiro, A.R., Castro, P.M.L., and Tiritan, M.E. (2017). Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction. Symmetry, 9.","DOI":"10.3390\/sym9090196"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"IUPAC (1996). Basic terminology of stereochemistry. Pure Appl. Chem., 68, 2193\u20132222.","DOI":"10.1351\/pac199668122193"},{"key":"ref_16","unstructured":"Testa, B., Caldwell, J., and Kisak\u00fcrek, M.V. (2014). Organic Stereochemistry: Guiding Principles and Biomedicinal Relevance, Wiley-VCH."},{"key":"ref_17","unstructured":"Solomons, T.W.G. (2011). Organic Chemistry, John Wiley & Sons, Inc.. [10th ed.]."},{"key":"ref_18","unstructured":"Allenmark, S. (1991). Chromatographic Enantioseparation: Methods and Applications, Ellis Horwood Ltd.. [2nd ed.]."},{"key":"ref_19","unstructured":"Eliel, E.L., and Wilen, S.H. (1994). Stereochemistry of Organic Compounds, John Wiley & Sons, Inc."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Tiritan, M.E., Ribeiro, A.R., Fernandes, C., and Pinto, M.M.M. (2016). Chiral Pharmaceuticals. Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, Inc.","DOI":"10.1002\/0471238961.1608011823092009.a01.pub2"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2012","DOI":"10.1021\/ed084p2012","article-title":"Unequal activities of enantiomers via biological receptors: Examples of chiral drug, pesticide, and fragrance molecules","volume":"84","author":"Mannschreck","year":"2007","journal-title":"J. Chem. Educ."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1590\/S0100-40421997000600015","article-title":"Drugs and chirality: A brief overview","volume":"20","author":"Lima","year":"1997","journal-title":"Quim. Nova"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2064","DOI":"10.2174\/092986709788682173","article-title":"Homochiral drugs: A demanding tendency of the pharmaceutical industry","volume":"16","author":"Nunez","year":"2009","journal-title":"Curr. Med. Chem."},{"key":"ref_24","unstructured":"Wainer, I.W., and Drayer, D.E. (1993). Drug Stereochemistry: Analytical Methods and Pharmacology (Clinical Pharmacology, No 18), Marcel Dekker. [2nd ed.]."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Gal, J. (2006). Chiral drugs from a historical point of view. Chirality in Drug Research, Wiley-VCH Verlag GmbH & Co. KGaA.","DOI":"10.1002\/9783527609437.ch1"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.ecoenv.2012.10.009","article-title":"Enantioselective biodegradation of pharmaceuticals, alprenolol and propranolol, by an activated sludge inoculum","volume":"87","author":"Ribeiro","year":"2013","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1007\/s10311-012-0383-1","article-title":"Enantioselective HPLC analysis and biodegradation of atenolol, metoprolol and fluoxetine","volume":"11","author":"Ribeiro","year":"2013","journal-title":"Environ. Chem. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1016\/j.jchromb.2016.06.026","article-title":"Integrated liquid chromatography method in enantioselective studies: Biodegradation of ofloxacin by an activated sludge consortium","volume":"1029\u20131030","author":"Maia","year":"2016","journal-title":"J. Chromatogr. B"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/j.jhazmat.2015.01.020","article-title":"Removal of fluoxetine and its effects in the performance of an aerobic granular sludge sequential batch reactor","volume":"287","author":"Moreira","year":"2015","journal-title":"J. Hazard. Mater."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1016\/j.ibiod.2016.09.009","article-title":"Treatment of a simulated wastewater amended with a chiral pharmaceuticals mixture by an aerobic granular sludge sequencing batch reactor","volume":"115","author":"Amorim","year":"2016","journal-title":"Int. Biodeterior. Biodegrad."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5443","DOI":"10.1021\/es060817d","article-title":"Influence of pH on the stereoselective degradation of the fungicides epoxiconazole and cyproconazole in soils","volume":"40","author":"Buerge","year":"2006","journal-title":"Environ. Sci. Technol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"7688","DOI":"10.1021\/acs.jafc.6b02961","article-title":"Effects of engineered nanoparticles on the enantioselective transformation of metalaxyl agent and commercial metalaxyl in agricultural soils","volume":"64","author":"Liang","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1612","DOI":"10.1016\/j.jiec.2013.08.008","article-title":"Mathematical model and experimental validation of the synergistic effect of selective enantioseparation of (S)-amlodipine from pharmaceutical wastewater using a HFSLM","volume":"20","author":"Sunsandee","year":"2014","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3396","DOI":"10.1002\/ejoc.201101769","article-title":"Synthesis and Preliminary Structural and Binding Characterization of New Enantiopure Crown Ethers Containing an Alkyl Diarylphosphinate or a Proton-Ionizable Diarylphosphinic Acid Unit","volume":"2012","author":"Farkas","year":"2012","journal-title":"Eur. J. Org. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"9957","DOI":"10.1002\/anie.201403145","article-title":"Functionalized graphene as a gatekeeper for chiral molecules: An alternative concept for chiral separation","volume":"53","author":"Hauser","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"9516","DOI":"10.1021\/acsami.5b00755","article-title":"Role of Chirality and macroring in imprinted polymers with enantiodiscriminative power","volume":"7","author":"Kupai","year":"2015","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1846","DOI":"10.1016\/j.tetasy.2006.06.026","article-title":"Enantiomer separation by enantioselective inclusion complexation\u2013organic solvent nanofiltration","volume":"17","author":"Ghazali","year":"2006","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"36884","DOI":"10.1038\/srep36884","article-title":"Completely chiral optical force for enantioseparation","volume":"6","author":"Rukhlenko","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1002\/(SICI)1520-667X(1999)11:6<475::AID-MCS10>3.0.CO;2-M","article-title":"Stopped-flow multidimensional gas chromatography: A new method for the determination of enantiomerization barriers","volume":"11","author":"Reich","year":"1999","journal-title":"J. Microcolumn Sep."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1016\/S0021-9673(99)01301-1","article-title":"Enantioselective stopped-flow multidimensional gas chromatography: Determination of the inversion barrier of 1-chloro-2,2-dimethylaziridine","volume":"892","author":"Reich","year":"2000","journal-title":"J. Chromatogr. A"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1002\/(SICI)1520-636X(1998)10:4<316::AID-CHIR5>3.0.CO;2-5","article-title":"Determination of the rotational barriers of atropisomeric polychlorinated biphenyls (PCBs) by a novel stopped-flow multidimensional gas chromatographic technique","volume":"10","author":"Schurig","year":"1998","journal-title":"Chirality"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/0021-9673(94)80367-6","article-title":"Evolution of chiral stationary phase design in the Pirkle laboratories","volume":"666","author":"Welch","year":"1994","journal-title":"J. Chromatogr. A"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"940","DOI":"10.1002\/ijch.201600089","article-title":"Gas Chromatographic Enantiomer Separation of Polychlorinated Biphenyls (PCBs): Methods, Metabolisms, Enantiomeric Composition in Environmental Samples and their Interpretation","volume":"56","author":"Vetter","year":"2016","journal-title":"Isr. J. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Vetter, W., and Bester, K. (2006). Gas chromatographic enantioseparation of chiral pollutants-techniques and results. Chiral Anal., 131\u2013213.","DOI":"10.1016\/B978-044451669-5\/50006-5"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"626","DOI":"10.1021\/ac202892w","article-title":"Chiral separations: A review of current topics and trends","volume":"84","author":"Ward","year":"2012","journal-title":"Anal. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1016\/S1359-6446(05)03407-0","article-title":"Enantioselective chromatography in drug discovery","volume":"10","author":"Zhang","year":"2005","journal-title":"Drug Discov. Today"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4712","DOI":"10.1021\/ac1010926","article-title":"Chiral Separations: Fundamental Review 2010","volume":"82","author":"Ward","year":"2010","journal-title":"Anal. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1093\/chromsci\/30.3.67","article-title":"Chiral separations by high-performance liquid chromatography","volume":"30","author":"Taylor","year":"1992","journal-title":"J. Chromatogr. Sci."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1016\/S0731-7085(01)00652-5","article-title":"Pharmaceutical and biomedical applications of enantioseparations using liquid chromatographic techniques","volume":"27","author":"Haginaka","year":"2002","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"814","DOI":"10.1016\/j.chroma.2009.10.022","article-title":"Chiral recognition by enantioselective liquid chromatography: Mechanisms and modern chiral stationary phases","volume":"1217","year":"2010","journal-title":"J. Chromatogr. A"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.jchromb.2014.02.049","article-title":"Enantioseparation of chiral pharmaceuticals in biomedical and environmental analyses by liquid chromatography: An overview","volume":"968","author":"Ribeiro","year":"2014","journal-title":"J. Chromatogr. B"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1007\/s10337-013-2469-8","article-title":"Small molecules as chromatographic tools for HPLC enantiomeric resolution: Pirkle-Type chiral stationary phases evolution","volume":"76","author":"Fernandes","year":"2013","journal-title":"Chromatographia"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/j.jchromb.2008.05.022","article-title":"Recent progresses in protein-based chiral stationary phases for enantioseparations in liquid chromatography","volume":"875","author":"Haginaka","year":"2008","journal-title":"J. Chromatogr. B"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1016\/j.talanta.2010.04.056","article-title":"A column-switching method for quantification of the enantiomers of omeprazole in native matrices of waste and estuarine water samples","volume":"82","author":"Barreiro","year":"2010","journal-title":"Talanta"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2865","DOI":"10.1016\/j.chroma.2011.02.064","article-title":"Direct injection of native aqueous matrices by achiral\u2013chiral chromatography ion trap mass spectrometry for simultaneous quantification of pantoprazole and lansoprazole enantiomers fractions","volume":"1218","author":"Barreiro","year":"2011","journal-title":"J. Chromatogr. A"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.aca.2015.02.016","article-title":"Tutorial review on validation of liquid chromatography\u2013mass spectrometry methods: Part II","volume":"870","author":"Kruve","year":"2015","journal-title":"Anal. Chim. Acta"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1016\/j.chroma.2014.06.099","article-title":"Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry","volume":"1363","author":"Ribeiro","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3499","DOI":"10.1007\/s00216-015-8543-3","article-title":"Simultaneous determination of chiral pesticide flufiprole enantiomers in vegetables, fruits, and soil by high-performance liquid chromatography","volume":"407","author":"Tian","year":"2015","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_59","first-page":"1081","article-title":"Strategy for correction of matrix effect on the determination of pesticides in water bodies using SPME-GC-FID","volume":"28","author":"Silva","year":"2017","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2529","DOI":"10.1021\/es981014w","article-title":"Occurrence and environmental behavior of the chiral pharmaceutical drug ibuprofen in surface waters and in wastewater","volume":"33","author":"Buser","year":"1999","journal-title":"Environ. Sci. Technol."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"9244","DOI":"10.1021\/es047965t","article-title":"Use of the chiral pharmaceutical propranolol to identify sewage discharges into surface waters","volume":"39","author":"Fono","year":"2005","journal-title":"Environ. Sci. Technol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1016\/j.chroma.2012.09.090","article-title":"Chiral analysis of metoprolol and two of its metabolites, \u03b1-hydroxymetoprolol and deaminated metoprolol, in wastewater using liquid chromatography\u2013tandem mass spectrometry","volume":"1269","author":"Barclay","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1002\/chir.22172","article-title":"A new chiral residue analysis method for triazole fungicides in water using dispersive liquid-liquid microextraction (DLLME)","volume":"25","author":"Luo","year":"2013","journal-title":"Chirality"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"6381","DOI":"10.1007\/s00216-016-9753-z","article-title":"Solid-phase extraction combined with dispersive liquid-liquid microextraction and chiral liquid chromatography-tandem mass spectrometry for the simultaneous enantioselective determination of representative proton-pump inhibitors in water samples","volume":"408","author":"Zhao","year":"2016","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1016\/j.talanta.2014.11.016","article-title":"Enantioselective determination of representative profens in wastewater by a single-step sample treatment and chiral liquid chromatography-tandem mass spectrometry","volume":"134","author":"Caballo","year":"2015","journal-title":"Talanta"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.aca.2015.03.039","article-title":"Determination of chiral pharmaceuticals and illicit drugs in wastewater and sludge using microwave assisted extraction, solid-phase extraction and chiral liquid chromatography coupled with tandem mass spectrometry","volume":"882","author":"Evans","year":"2015","journal-title":"Anal. Chim. Acta"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1002\/chir.22151","article-title":"Enantiomeric fraction determination of 2-arylpropionic acids in a package plant membrane bioreactor","volume":"25","author":"Hashim","year":"2013","journal-title":"Chirality"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1016\/j.scitotenv.2013.03.043","article-title":"Spatial and temporal occurrence of pharmaceuticals and illicit drugs in the aqueous environment and during wastewater treatment: New developments","volume":"454\u2013455","author":"Baker","year":"2013","journal-title":"Sci. Total Environ."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1016\/j.scitotenv.2012.02.019","article-title":"Estimation of community-wide drugs use via stereoselective profiling of sewage","volume":"423","author":"Baker","year":"2012","journal-title":"Sci. Total Environ."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1016\/j.chroma.2013.06.006","article-title":"Enantiomeric analysis of polycyclic musks in water by chiral gas chromatography\u2013tandem mass spectrometry","volume":"1303","author":"Wang","year":"2013","journal-title":"J. Chromatogr. A"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"5859","DOI":"10.1007\/s00216-013-6900-7","article-title":"Multi-residue enantiomeric analysis of pharmaceuticals and their active metabolites in the Guadalquivir River basin (South Spain) by chiral liquid chromatography coupled with tandem mass spectrometry","volume":"405","year":"2013","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1933","DOI":"10.1016\/j.chemosphere.2012.10.033","article-title":"Chiral signature of venlafaxine as a marker of biological attenuation processes","volume":"90","author":"Li","year":"2013","journal-title":"Chemosphere"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1016\/j.chemosphere.2012.02.074","article-title":"Field and laboratory studies of the fate and enantiomeric enrichment of venlafaxine and O-desmethylvenlafaxine under aerobic and anaerobic conditions","volume":"88","author":"Gasser","year":"2012","journal-title":"Chemosphere"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1751","DOI":"10.1007\/s00216-012-5976-9","article-title":"Enantiomeric determination of azole antifungals in wastewater and sludge by liquid chromatography\u2013tandem mass spectrometry","volume":"403","author":"Huang","year":"2012","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"5551","DOI":"10.1016\/j.watres.2012.07.033","article-title":"Fate of pharmaceuticals in rivers: Deriving a benchmark dataset at favorable attenuation conditions","volume":"46","author":"Kunkel","year":"2012","journal-title":"Water Res."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.chroma.2012.06.012","article-title":"Using chiral liquid chromatography quadrupole time-of-flight mass spectrometry for the analysis of pharmaceuticals and illicit drugs in surface and wastewater at the enantiomeric level","volume":"1249","author":"Bagnall","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.1021\/es203113y","article-title":"Enantiomeric profiling of chiral drugs in wastewater and receiving waters","volume":"46","author":"Baker","year":"2012","journal-title":"Environ. Sci. Technol."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.jpba.2011.12.029","article-title":"Comparative HPLC methods for \u03b2-blockers separation using different types of chiral stationary phases in normal phase and polar organic phase elution modes. Analysis of propranolol enantiomers in natural waters","volume":"62","author":"Sierra","year":"2012","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"860","DOI":"10.1002\/chir.22084","article-title":"Simultaneous enantiomeric determination of propranolol, metoprolol, pindolol, and atenolol in natural waters by HPLC on new polysaccharide-based stationary phase using a highly selective molecularly imprinted polymer extraction","volume":"24","author":"Sierra","year":"2012","journal-title":"Chirality"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"4746","DOI":"10.1016\/j.chroma.2011.05.046","article-title":"Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples","volume":"1218","author":"Hashim","year":"2011","journal-title":"J. Chromatogr. A"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"5587","DOI":"10.1016\/j.chroma.2011.06.024","article-title":"Trace analysis of fluoxetine and its metabolite norfluoxetine. Part I: Development of a chiral liquid chromatography\u2013tandem mass spectrometry method for wastewater samples","volume":"1218","author":"Barclay","year":"2011","journal-title":"J. Chromatogr. A"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"4575","DOI":"10.1016\/j.chroma.2010.04.073","article-title":"Enantiomeric analysis of drugs of abuse in wastewater by chiral liquid chromatography coupled with tandem mass spectrometry","volume":"1217","author":"Kondakal","year":"2010","journal-title":"J. Chromatogr. A"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.chemosphere.2008.12.008","article-title":"Assessment of the pharmaceutical active compounds removal in wastewater treatment systems at enantiomeric level. Ibuprofen and naproxen","volume":"75","author":"Matamoros","year":"2009","journal-title":"Chemosphere"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.chroma.2006.07.033","article-title":"Stereoisomer quantification of the -blocker drugs atenolol, metoprolol, and propranolol in wastewaters by chiral high-performance liquid chromatography-tandem mass spectrometry","volume":"1131","author":"Nikolai","year":"2006","journal-title":"J. Chromatogr. A"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"7257","DOI":"10.1021\/es061308e","article-title":"Attenuation of Wastewater-Derived Contaminants in an Effluent-Dominated River","volume":"40","author":"Fono","year":"2006","journal-title":"Environ. Sci. Technol."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1016\/j.chemosphere.2013.09.118","article-title":"Enantioselective quantification of fluoxetine and norfluoxetine by HPLC in wastewater effluents","volume":"95","author":"Ribeiro","year":"2014","journal-title":"Chemosphere"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.jchromb.2016.04.033","article-title":"Source discrimination of drug residues in wastewater: The case of salbutamol","volume":"1023\u20131024","author":"Depaolini","year":"2016","journal-title":"J. Chromatogr. B"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"8890","DOI":"10.1007\/s11356-013-1862-z","article-title":"Chiral profiling of azole antifungals in municipal wastewater and recipient rivers of the Pearl River Delta, China","volume":"20","author":"Huang","year":"2013","journal-title":"Environ. Sci. Pollut. R."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1002\/chir.22258","article-title":"Distinct enantiomeric signals of ibuprofen and naproxen in treated wastewater and sewer overflow","volume":"26","author":"Khan","year":"2014","journal-title":"Chirality"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/j.watres.2016.03.010","article-title":"Enantiomeric fractionation as a tool for quantitative assessment of biodegradation: The case of metoprolol","volume":"95","author":"Souchier","year":"2016","journal-title":"Water Res."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"2671","DOI":"10.1002\/etc.2741","article-title":"Occurrence and behavior of the chiral anti-inflammatory drug naproxen in an aquatic environment","volume":"33","author":"Suzuki","year":"2014","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1016\/j.envpol.2016.04.103","article-title":"Enantioselective degradation of amphetamine-like environmental micropollutants (amphetamine, methamphetamine, MDMA and MDA) in urban water","volume":"215","author":"Evans","year":"2016","journal-title":"Environ. Pollut."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"368","DOI":"10.1016\/j.envpol.2017.06.070","article-title":"Enantiomeric profiling of a chemically diverse mixture of chiral pharmaceuticals in urban water","volume":"230","author":"Evans","year":"2017","journal-title":"Environ. Pollut."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.scitotenv.2016.03.053","article-title":"Characterization of pharmaceutically active compounds in Dongting Lake, China: Occurrence, chiral profiling and environmental risk","volume":"557\u2013558","author":"Ma","year":"2016","journal-title":"Sci. Total Environ."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1016\/j.scitotenv.2016.11.059","article-title":"Critical evaluation of monitoring strategy for the multi-residue determination of 90 chiral and achiral micropollutants in effluent wastewater","volume":"579","author":"Petrie","year":"2017","journal-title":"Sci. Total Environ."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/02772240410001665580","article-title":"Analysis of the chiral pollutants by chromatography","volume":"86","author":"Ali","year":"2004","journal-title":"Toxicol. Environ. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/0025-326X(91)90142-F","article-title":"Gas chromatographic separation of the enantiomers of marine organic pollutants distribution of -HCH enantiomers in the North Sea","volume":"22","author":"Faller","year":"1991","journal-title":"Mar. Pollut. Bull."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1002\/chir.530050522","article-title":"Enantioselective and nonenantioselective degradation of organic pollutants in the marine ecosystem","volume":"5","author":"Faller","year":"1993","journal-title":"Chirality"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"2127","DOI":"10.1021\/es00035a009","article-title":"Gas chromatographic separation of the enantiomers of marine pollutants. 4. Fate of hexachlorocyclohexane isomers in the Baltic and North Sea","volume":"26","author":"Faller","year":"1992","journal-title":"Environ. Sci. Technol."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/j.chroma.2011.12.084","article-title":"Trace analysis of fluoxetine and its metabolite norfluoxetine. Part II: Enantioselective quantification and studies of matrix effects in raw and treated wastewater by solid phase extraction and liquid chromatography\u2013tandem mass spectrometry","volume":"1227","author":"Barclay","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"9085","DOI":"10.1007\/s00216-015-9075-6","article-title":"Multi-residue enantiomeric analysis of human and veterinary pharmaceuticals and their metabolites in environmental samples by chiral liquid chromatography coupled with tandem mass spectrometry detection","volume":"407","year":"2015","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/j.aca.2016.05.051","article-title":"Enantioselective simultaneous analysis of selected pharmaceuticals in environmental samples by ultrahigh performance supercritical fluid based chromatography tandem mass spectrometry","volume":"934","author":"Thomas","year":"2016","journal-title":"Anal. Chim. Acta"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1016\/j.watres.2009.09.056","article-title":"Loadings, trends, comparisons, and fate of achiral and chiral pharmaceuticals in wastewaters from urban tertiary and rural aerated lagoon treatments","volume":"44","author":"MacLeod","year":"2010","journal-title":"Water Res."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.chroma.2007.09.010","article-title":"Stereoisomer analysis of wastewater-derived b-blockers, selective serotonin re-uptake inhibitors, and salbutamol by high-performance liquid chromatography-tandem mass spectrometry","volume":"1170","author":"MacLeod","year":"2007","journal-title":"J. Chromatogr. A"},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1002\/jms.3904","article-title":"Simultaneous enantiomeric analysis of pharmacologically active compounds in environmental samples by chiral LC\u2013MS\/MS with a macrocyclic antibiotic stationary phase","volume":"52","year":"2017","journal-title":"J. Mass Spectrom."},{"key":"ref_106","first-page":"117","article-title":"Analytical separation of enantiomers by gas chromatography on chiral stationary phases","volume":"52","author":"Schurig","year":"2015","journal-title":"Adv. Chromatogr."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/j.chroma.2017.07.078","article-title":"Chiral stationary phase optimized selectivity liquid chromatography: A strategy for the separation of chiral isomers","volume":"1515","author":"Hegade","year":"2017","journal-title":"J. Chromatogr. A"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"847","DOI":"10.1016\/j.trac.2008.08.010","article-title":"Enantiomeric determination of chiral persistent organic pollutants and their metabolites","volume":"27","author":"Eljarrat","year":"2008","journal-title":"TrAC Trends Anal. Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"1713","DOI":"10.1016\/j.chroma.2008.11.084","article-title":"Recent advances in gas chromatography for solid and liquid stationary phases containing metal ions","volume":"1216","author":"Rykowska","year":"2009","journal-title":"J. Chromatogr. A"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1016\/S0021-9673(99)01104-8","article-title":"Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns","volume":"866","author":"Wong","year":"2000","journal-title":"J. Chromatogr. A"},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"527","DOI":"10.1016\/j.watres.2017.08.003","article-title":"Chiral pharmaceuticals: A review on their environmental occurrence and fate processes","volume":"124","author":"Sanganyado","year":"2017","journal-title":"Water Res."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"1940","DOI":"10.1021\/es9607244","article-title":"Enantiomers of alfa-Hexachlorocyclohexane as Tracers of Air-Water Gas Exchange in Lake Ontario","volume":"31","author":"Ridal","year":"1997","journal-title":"Environ. Sci. Technol."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"843","DOI":"10.1016\/S0045-6535(01)00033-9","article-title":"Chiral analysis of organochlorine pesticides in Alabama soils","volume":"45","author":"Wiberg","year":"2001","journal-title":"Chemosphere"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"1421","DOI":"10.1002\/etc.5620220702","article-title":"Variations in \u03b1-hexachlorocyclohexane enantiomer ratios in relation to microbial activity in a temperate estuary","volume":"22","author":"Padma","year":"2003","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"3457","DOI":"10.1021\/es980317n","article-title":"Occurrence and Behavior of Pesticides in Rainwater, Roof Runoff, and Artificial Stormwater Infiltration","volume":"32","author":"Bucheli","year":"1998","journal-title":"Environ. Sci. Technol."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1007\/128_2013_454","article-title":"Terms for the quantitation of a mixture of stereoisomers","volume":"340","author":"Schurig","year":"2013","journal-title":"Top. Curr. Chem."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1016\/j.talanta.2013.10.043","article-title":"Fast, simple and efficient supramolecular solvent-based microextraction of mecoprop and dichlorprop in soils prior to their enantioselective determination by liquid chromatography-tandem mass spectrometry","volume":"119","author":"Caballo","year":"2014","journal-title":"Talanta"},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"7033","DOI":"10.1016\/j.chroma.2009.08.060","article-title":"Pharmaceutical trace analysis in aqueous environmental matrices by liquid chromatography\u2013ion trap tandem mass spectrometry","volume":"1216","author":"Madureira","year":"2009","journal-title":"J. Chromatogr. A"},{"key":"ref_119","unstructured":"Verbruggen, E.M.J., and Van den Brink, P.J. (2010). Review of Recent Literature Concerning Mixture Toxicity of Pesticides to Aquatic Organisms, National Institute for Public Health and the Environment. RIVM Report 601400001\/2010."},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1016\/j.envpol.2014.05.021","article-title":"Spatial and temporal distribution of chiral pesticides in Calanus spp. from three Arctic fjords","volume":"192","author":"Carlsson","year":"2014","journal-title":"Environ. Pollut."},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"28837","DOI":"10.1029\/96JD02352","article-title":"Air-water gas exchange of hexachlorocyclohexanes (HCHs) and the enantiomers of c-HCH in arctic regions","volume":"101","author":"Jantunen","year":"1996","journal-title":"J. Geophys. Res."},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1139\/y76-088","article-title":"Differing estrogenic activities for the enantiomers of o,p\u2032-DDT in immature female rats","volume":"54","author":"McBlain","year":"1976","journal-title":"Can. J. Physiol. Pharmacol."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"2668","DOI":"10.1021\/es0202412","article-title":"Enantioselective degradation of metalaxyl in soils: Chiral preference changes with soil pH","volume":"37","author":"Buerge","year":"2003","journal-title":"Environ. Sci. Technol."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"626","DOI":"10.1021\/es970652w","article-title":"Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in switzerland","volume":"32","author":"Buser","year":"1998","journal-title":"Environ. Sci. Technol."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/S0045-6535(02)00080-2","article-title":"Sources of pesticides in surface waters in Switzerland: pesticide load through waste water treatment plants\u2013\u2013current situation and reduction potential","volume":"48","author":"Gerecke","year":"2002","journal-title":"Chemosphere"},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"2271","DOI":"10.1016\/S0045-6535(97)00039-8","article-title":"Bromocyclen contamination of surface water, waste water and fish from northern germany, and gas chromatographic chiral separation","volume":"34","author":"Bethan","year":"1997","journal-title":"Chemosphere"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/j.chroma.2003.08.102","article-title":"Determination of atropisomeric and planar polychlorinated biphenyls, their enantiomeric fractions and tissue distribution in grey seals using comprehensive 2D gas chromatography","volume":"1019","author":"Harju","year":"2003","journal-title":"J. Chromatogr. A"},{"key":"ref_128","unstructured":"UNEP, U.n.e.p.C. (2001, January 22). TREATIES-4. Stockholm convention on persistent organic pollutants. Adoption of amendments to Annexes A, B and C by decisions SC-4\/10, 4\/11, 4\/12, 4\/13, 4\/14, 4\/15, 4\/16, 4\/17 and 4\/18. Proceedings of the Conference of Plenipotentiaries, Stockholm, Sweden."},{"key":"ref_129","unstructured":"EU-Directive (2013). Directive 2013\/39\/EU of the European Parliament and of the Council of 12 August 2013 amending Directives 2000\/60\/EC and 2008\/105\/EC as regards priority substances in the field of water policy. Off. J. Eur. Union, L.226, 1\u201317."},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"3845","DOI":"10.1021\/ac980064g","article-title":"Enantioselective gas chromatography\/mass spectrometry of methylsulfonyl PCBs with application to arctic marine mammals","volume":"70","author":"Wiberg","year":"1998","journal-title":"Anal. Chem."},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"245","DOI":"10.3109\/10408444.2014.999365","article-title":"Metabolism and metabolites of polychlorinated biphenyls (PCBs)","volume":"45","author":"Grimm","year":"2015","journal-title":"Crit. Rev. Toxicol."},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/j.chemosphere.2017.03.058","article-title":"PCBs and OCPs in human milk in Eastern Siberia, Russia: Levels, temporal trends and infant exposure assessment","volume":"178","author":"Mamontova","year":"2017","journal-title":"Chemosphere"},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"855","DOI":"10.1016\/j.envint.2009.03.005","article-title":"External exposure and bioaccumulation of PCBs in humans living in a contaminated urban environment","volume":"36","author":"Czub","year":"2010","journal-title":"Environ. Int."},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1021\/es9807385","article-title":"Congener specific determination and enantiomeric ratios of chiral polychlorinated biphenyls in striped dolphins (stenella coeruleoalba) from the mediterranean sea","volume":"33","author":"Reich","year":"1999","journal-title":"Environ. Sci. Technol."},{"key":"ref_135","doi-asserted-by":"crossref","first-page":"2542","DOI":"10.1002\/etc.5620211204","article-title":"Concentrations and enantiomer fractions of organochlorine compounds in baltic species hit by reproductive impairment","volume":"21","author":"Wiberg","year":"2002","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_136","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1039\/b300949a","article-title":"Enantiomeric signatures of chiral polychlorinated biphenyl atropisomers in livers of harbour porpoises (Phocoena phocoena) from the southern North Sea","volume":"5","author":"Chu","year":"2003","journal-title":"J. Environ. Monit."},{"key":"ref_137","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1002\/jhrc.1240190207","article-title":"Multidimensional gas chromatographic separation of selected PCB atropisomers in technical formulations and sediments","volume":"19","author":"Novakovsky","year":"1996","journal-title":"J. High Resolut. Chromatogr."},{"key":"ref_138","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/0021-9673(95)00846-2","article-title":"Enantioselective analysis of chiral polychlorinated biphenyls in sediment samples by multidimensional gas chromatography-electron-capture detection after steam distillation-solvent extraction and sulfur removal","volume":"723","author":"Glausch","year":"1996","journal-title":"J. Chromatogr. A"},{"key":"ref_139","doi-asserted-by":"crossref","unstructured":"Lee, I., Gopalan, A.I., and Lee, K.P. (2016). Enantioselective determination of polycyclic musks in river and wastewater by GC\/MS\/MS. Int. J. Env. Res. Public Health, 13.","DOI":"10.3390\/ijerph13030349"},{"key":"ref_140","doi-asserted-by":"crossref","first-page":"987","DOI":"10.1016\/j.chemosphere.2004.07.020","article-title":"Considerations about the enantioselective transformation of polycyclic musks in wastewater, treated wastewater and sewage sludge and analysis of their fate in a sequencing batch reactor plant","volume":"57","author":"Berset","year":"2004","journal-title":"Chemosphere"},{"key":"ref_141","doi-asserted-by":"crossref","first-page":"1518","DOI":"10.1016\/j.chemosphere.2010.11.018","article-title":"A review of personal care products in the aquatic environment: Environmental concentrations and toxicity","volume":"82","author":"Brausch","year":"2011","journal-title":"Chemosphere"},{"key":"ref_142","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/0048-9697(95)04345-2","article-title":"Air-water gas exchange and evidence for metabolism of hexachlorocyclohexanes in Resolute Bay, N.W.T.","volume":"160\u2013161","author":"Falconer","year":"1995","journal-title":"Sci. Total Environ."},{"key":"ref_143","doi-asserted-by":"crossref","first-page":"218","DOI":"10.1007\/s002449900370","article-title":"Organochlorine pesticides and enantiomers of chiral pesticides in arctic ocean water","volume":"35","author":"Jantunen","year":"1998","journal-title":"Arch. Environ. Contam. Toxicol."},{"key":"ref_144","doi-asserted-by":"crossref","first-page":"4965","DOI":"10.1021\/es0620787","article-title":"Enantioselective degradation of organochlorine pesticides in background soils: Variability in field and laboratory studies","volume":"41","author":"Stroud","year":"2007","journal-title":"Environ. Sci. Technol."},{"key":"ref_145","doi-asserted-by":"crossref","first-page":"2153","DOI":"10.1021\/es062218c","article-title":"Concentrations and chiral signatures of polychlorinated biphenyls in outdoor and indoor air and soil in a major U.K. conurbation","volume":"41","author":"Jamshidi","year":"2007","journal-title":"Environ. Sci. Technol."}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/9\/10\/215\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:46:32Z","timestamp":1760208392000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/9\/10\/215"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,10,3]]},"references-count":145,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2017,10]]}},"alternative-id":["sym9100215"],"URL":"https:\/\/doi.org\/10.3390\/sym9100215","relation":{},"ISSN":["2073-8994"],"issn-type":[{"value":"2073-8994","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,10,3]]}}}