Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review
Abstract
:1. Introduction
2. Basic Concepts of Chirality
3. Analytical Methodologies for Enantioseparation of Chiral Bioactive Compounds
4. Chiral Bioactive Compounds of Environmental Concern
4.1. Illicit Drugs and Pharmaceuticals
Multi-Class Enantioselective Analysis
4.2. Environmental Chiral Analysis of Pesticides, PCBs and PCMs
4.2.1. Pesticides
4.2.2. Polychlorinated Biphenyls (PCBs)
4.2.3. Polycyclic Musks (PCMs)
5. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Chiral Compounds | Analytical Method | Location/Matrix | Concentration/ER, EF | Ref. |
---|---|---|---|---|
Amphetamine Methamphetamine MDMA MDA | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm i.d.); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. | United Kingdom Influent (IWW) and effluent (EWW) wastewater; River water. | IWW: EF = 0.6; EWW: EF = 0.4; IWW: EF > 0.5; EWW: EF > 0.5; IWW: EF < 0.5; EWW: EF < 0.5; IWW: EF > 0.5; EWW: EF < 0.5. | [92] |
Amphetamine Methamphetamine MDMA MDA MDEA Ephedrine Norephedrine | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm i.d.); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. | England Influent (IWW) and effluent (EWW) wastewater River water (RW): 6 locations near the WWTP discharge zone | 17.4–3112.5 ng L−1 (IWW); 4.3–145.2 ng L−1 (EWW); 0.3–4.3 ng L−1 (SW); 0.6–70.3 ng L−1 (IWW); 0.4–1.3 ng L−1 (EWW); 0.3–0.4 ng L−1 (SW); 7.2–32.4 ng L−1 (IWW); 6.3–24.5 ng L−1 (EWW); 0.9–1.9 ng L−1 (SW); 0.7–455.4 ng L−1 (IWW); 0.6–177.7 ng L−1 (EWW); 0.5–24.8 ng L−1 (SW); 1.4 ng L−1 (IWW); n.d. (EWW); n.d. (SW); 8.7–1979.5 ng L−1 (IWW); 5.3–265 ng L−1 (EWW); 6.3–28.9 ng L−1 (SW); 15–99.9 ng L−1 (IWW); n.d. (EWW); n.d. (SW). | [68] |
Amphetamine Methamphetamine MDMA MDA Ephedrine Pseudoephedrine | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm i.d.); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. | England Wastewater influent and effluent | EF = 0.52–0.84; EF ≥ 0.5; EF = 0.68 (mean); EF > 0.5; EF = 0.81–0.96; - | [69] |
Amphetamine Methamphetamine MDMA MDA Ephedrine Pseudoephedrine Norephedrine Alprenolol Atenolol Citalopram Desmethylcitalopram Desmethylvenlafaxine Fluoxetine Mirtazapine Metoprolol Propranolol Salbutamol Sotalol Tramadol Venlafaxine | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm i.d.); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. Chirobiotic V column, (250 × 2.1 mm, i.d. 5 µm) with a Chirobiotic V guard column (20 × 1.0 mm, i.d. 5 µm); Methanol (4 mM ammonium acetate, 0.005% formic acid) | Not referred Influent (IWW) and effluent (EWW) wastewater; Sludge (Sl.). | IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.7; IWW: EF = 0.6; EWW: EF = 0.5; Sl.: EF = 0.5; IWW: EF = 0.7; EWW: EF = 0.9; Sl.: EF = 0.4; IWW: EF = 0.6; EWW: EF = 0.5; Sl.: EF = 0.3; IWW: EF = 0; EWW: EF = 0; Sl.: EF = n.d.; IWW: EF = 1; EWW: EF = 0.2; Sl.: EF = n.d.; IWW: EF = 0; EWW: EF = 0.3; Sl.: EF = 0.1; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.7; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.4; IWW: EF = 0.6; EWW: EF = 0.7; Sl.: EF = 0.6; IWW: EF = 1; EWW: EF = n.d.; Sl.: EF = 0.6; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.5; IWW: EF = 0.7; EWW: EF = 0.7; Sl.: EF = 0.7; IWW: EF = 0.3; EWW: EF = 0.2; Sl.: EF = 0.5; IWW: EF = 0.3; EWW: EF = n.d.; Sl.: EF = 0.4; IWW: EF = 0.4; EWW: EF = 0.4; Sl.: EF = 0.5; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = n.d.; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.5; IWW: EF = 0.7; EWW: EF = 0.7; Sl.: EF = 0.7; IWW: EF = 0.5; EWW: EF = 0.5; Sl.: EF = 0.5; | [66] |
MDMA Atenolol Citalopram Desmethylcitalopram Fluoxetine Mirtazapine Metoprolol Propranolol | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm); H2O-2-propanol (85:15, v/v) (1 mM ammonium acetate) Chirobiotic V column, (100 × 2.1 mm, i.d. 5 µm); Methanol (4 mM ammonium acetate, 0.005% formic acid) | Not referred Effluent wastewater. | EF showed temporal changes (0.24–0.38); EF did not show temporal changes; EF did not show temporal changes; EF did not show temporal changes; EF did not show temporal changes; EF did not show temporal changes; EF did not show temporal changes; EF did not show temporal changes. | [95] |
Amphetamine Methamphetamine MDMA MDA Alprenolol Atenolol Citalopram Desmethylcitalopram Desmethylvenlafaxine Fluoxetine Mirtazapine Metoprolol Propranolol Salbutamol Sotalol Venlafaxine | UPLC-MS/MS; Chiral-CBH column (100 mm × 2 mm i.d., 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm i.d.); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. Chirobiotic V column, (250 × 2.1 mm, i.d. 5 µm) with a Chirobiotic V guard column (20 × 1.0 mm, i.d. 5 µm); Methanol (4 mM ammonium acetate, 0.005% formic acid) | Not referred Influent (IWW) and effluent (EWW) wastewater; Sludge (Sl.). | IWW: EF = 0.64; EWW: EF = 0.42; IWW: EF = 0.89; EWW: EF = 0.63; IWW: EF = 0.36; EWW: EF = 0.22; IWW: EF = 0.59; EWW: EF = 0.42; IWW: EF = 0.51; EWW: EF = 0.48; IWW: EF = 0.50; EWW: EF = 0.54; IWW: EF = 1.0; EWW: EF = 1.0; IWW: EF = 0.26; EWW: EF = 0.10; IWW: EF = 0.57; EWW: EF = 0.52; IWW: EF = 0.69; EWW: EF = 0.62; IWW: EF = 0.25; EWW: EF = 0.19; IWW: EF = 0.33; EWW: EF = n.d.; IWW: EF = 0.46; EWW: EF = 0.41; IWW: EF = 0.65; EWW: EF = 0.57; IWW: EF = 0.50; EWW: EF = 0.50. Venlafaxine | [93] |
Ibuprofen Naproxen Fexofenadine Tetramisole Ketoprofen Aminorex Chloramphenicol 3-N-Dechloroethylifosfamide 10,11-dihydro-10-hydroxycarbamazepine Dihydroketoprofen Ifosfamide Praziquantel | LC-MS/MS Chiral-AGP (100 × 2 mm, i.d. 5 μm) column with a Chiral-AGP (10 × 2.0 mm, i.d. 5 μm) guard column; Aqueous solution of 10 mM ammonium acetate with 1% of acetonitrile, pH 6.7 | United Kingdom Effluent wastewater; River water (South West England). | EF = 0.65 EF = 0.92 EF = 0.55 EF = 0.50 - - - - - - - - | [101] |
Aminorex 2-hydroxyibuprofen Ibuprofen Imazalil Naproxen Ofloxacin Tetramisole Carprofen Chloramphenicol 3-N-dechloroethylifosfamide Flurbiprofen Ifosfamide Omeprazole Praziquantel Indoprofen | LC-MS/MS Polysaccharide amylose tris-3,5-dimethylphenylcarbamate column and a cellulose tris-(3-chloro-4-methylphenylcarbamate column (150 × 2.1 mm, i.d. 2.5 μm); CO2-methanol/acetonitrile/2-propanol, 1:1:1, v/v with 10 mM ammonium acetate and 0.1% ammonium hydroxide under a gradient program (in positive ionization); Polysaccharide amylose tris-3,5-dimethylphenylcarbamate column (150 × 2.1 mm, i.d. 2.5 μm); CO2-methanol with 0.1% ammonium hydroxide under a gradient program (in negative ionization). | Northern and Western Europe Influent and effluent wastewater. | EF = 0.4 (IWW) EF = 0.2 (IWW) EF = 1.0 (IWW) EF = 0 (IWW) EF = 1.0 (IWW and EWW) EF = 0 (IWW) EF = 0.6 (IWW and EWW) - - - - - - - - | [102] |
Carboxyibuprofen Chloramphenicol 2-hydroxyibuprofen Ibuprofen Ifosfamide Indoprofen Ketoprofen Naproxen Praziquantel | Chirobiotic T column (250 × 2.1 mm, i.d. 5 μm); Methanol-10 mM ammonium acetate (30/70, v/v), pH 4.2. | United Kingdom Influent and effluent wastewater; River water (South West England). | EF = 0.83 (IWW) - EF = 0.79 (IWW) EF = 1.0 (IWW) - - - EF = 1.0 (IWW) - | [105] |
MDMA MDA Amphetamine Methamphetamine Ephedrine Venlafaxine Atenolol | LC-MS/MS; Chiral-CBH column (100 mm × 2 mm, 5 μm) with a Chiral-CBH guard column (10 mm × 2.0 mm); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. | Location n.a.; River water; Influent and effluent wastewater (7 WWTPs using mainly activated sludge and trickling filters technologies). | IWW: <LOQ—455 ng L−1; EF = 0.68; EWW: <LOQ—115 ng L−1; EF = 0.78. IWW: 11.8—45.8 ng L−1; EF = 0.26–0.47; EWW: 12.3—19.0 ng L−1; EF = 0.4–0.58. IWW: <LOQ—3112.5 ng L−1; EF = 0.59–0.84; EWW: <LOQ—19.7 ng L−1; EF = 0.68–1.0. IWW: <LOQ—1.8 ng L−1; EF = 0.22–0.53; EWW: <LOQ; EF = 0.70–1.0. IWW: <LOQ—15171 ng L−1; EF = 0.81–1.0; EWW: <LOQ—84.1 ng L−1; EF = 0.72–1.0. IWW: 28.8–325.5 ng L−1; EF = 0.35–0.65; EWW: 25–222 ng L−1; EF = 0.46–0.69. IWW: 4288–19160 ng L−1; EF = 0.30–0.47; EWW: 1480–18831 ng L−1; EF = 0.40–0.61. | [77] |
Amphetamine Methamphetamine MDA MDMA Propranolol Atenolol Metoprolol Fluoxetine Venlafaxine | LC-MS/MS; Chiral-CBH column (100 × 2 mm, i.d. 5 µm) with a Chiral-CBH µm guard column (10 × 2.0 mm i.d., 5 µm); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 7.0. | United Kingdom River water (River Avon, Salford, Somerset). | <MQL; <MQL; <MQL; <MQL; <MQL; <MQL; <MQL; <MQL; <MQL. | [76] |
Amphetamine Methamphetamine MDA MDMA Propranolol Atenolol Metoprolol Fluoxetine Venlafaxine | LC-MS/MS; Chirobiotic V column, (250 × 4.6 mm, i.d. 5 µm) with a Chirobiotic V guard column (20 × 4.0 mm, i.d. 5 µm); Methanol containing 4 mM ammonium acetate and 0.005% formic acid. | United Kingdom River water (River Avon, Salford, Somerset); Effluent wastewater | EWW: <MQL; RW: <MQL; EWW: <MQL; RW: <MQL; EWW: <MQL; RW: n.d.; EWW: <MQL; RW: <MQL; EWW: EF = 0.43; RW: EF = 0.45; EWW: EF = 0.55; RW: EF = 0.47; EWW: EF = 0.54; RW: < MQL; EWW: EF = 0.43; RW: EF = 0.58; EWW: <MQL; RW: < MQL. | |
Amphetamine Methamphetamine MDA MDEA MDMA Ephedrine 1R,2S (−) Pseudophedrine 1S,2S (+) Norephedrine Venlafaxine | LC-MS/MS; Chiral-CBH column (100 mm × 2 mm, 5 µm) with a Chiral-CBH guard column (10 mm × 2.0 mm); H2O-2-propanol (90:10, v/v), 1 mM ammonium acetate, pH 5.0. | Location n.a. Wastewater influent and effluent (4 WWTPs). | IWW: (S)-form 24.2–155.2 ng L−1; (R)-form 39.5–212.9 ng L−1; EF = 0.54–0.62; EWW: n.d.; IWW: (S)- and (R)-forms n.d.; EWW: (S)-form n.d. - < MQL; (R)-form n.d.; n.d.; IWW: n.d. - < MQL; EWW: n.d.; IWW: E1 < MQL—5.5 ng L−1; E2 < MQL—13.9 ng L−1; EF = 0.53–0.72; EWW: E1 n.d.–4.0 ng L−1; E2 < MQL—10.0 ng L−1; EF = 0.71 IWW: 14.3–72.3 ng L−1; EWW: <MQL—14.8 ng L−1; IWW: 51.0–329.7 ng L−1; EWW: <MQL—27.7 ng L−1; n.d. IWW: E1 57.2–286.5 ng L−1; E2 56.7–343.8 ng L−1; EF = 0.45–0.50; EWW: E1 80.2–178.2 ng L−1; E2 123.7–248.3 ng L−1; EF = 0.37–0.48. | [82] |
Metoprolol Propranolol Atenolol Fluoxetine Venlafaxine Ibuprofen Flurbiprofen Naproxen | LC-MS/MS; Chirobiotic V column, (250 × 4.6 mm, i.d. 5 µm) with a Chirobiotic V guard column (20 × 4.0 mm, i.d. 5 µm); Chiralpak AD-RH column, (150 × 4.6 mm, i.d. 5 µm). | China Surface water (Dongting Lake). | 0.48–0.64 0.44–0.56 n.d. - 0.46–0.51 - n.d. - | [94] |
16 pharmaceuticals (analgesics, antibiotics, beta-agonists, psychiatric and cardiovascular drugs) and two metabolites | LC-MS/MS; Chirobiotic V (250 × 2.1 mm i.d., 5 μm) with a Chirobiotic V guard column (20 mm × 1.0 mm i.d., 5 μm); Methanol(4 mM ammonium acetate)-formic acid (99.95:0.005, v/v). | Spain Influent and effluent wastewaters; River water (24 sampling locations; Guadalquivir River basin). | [71] | |
Venlafaxine Fluoxetine Norfluoxetine Alprenolol Bisoprolol Metoprolol Propranolol Salbutamol | LC-MS/MS; Chirobiotic V column (150 mm × 2.1 mm i.d., 5 µm); Ethanol-10 mM ammonium acetate aqueous solution (92.5:7.5, v/v), pH 6.8. | Portugal Effluent wastewater from 3 WWTPs. | EF = 0.54–0.55 - - - - - - | [57] |
Salbutamol | LC-MS/MS; Chirobiotic V column (250 mm x 2.1 mm i.d., 5 µm); Methanol(4 mM ammonium acetate)-formic acid (99.95:0.005, v/v). | Italy 24-h raw wastewater composite samples from 2 WWTPs (Nosedo and San Rocco, Milan). | EF one-day peaks = 0.484 ± 0.019 EF regular = 0.452 ± 0.018. | [87] |
Atenolol Metoprolol Propranolol Sotalol Citalopram Paroxetine Naproxen Temazepan | LC-MS/MS; Chirobiotic V column (250 mm × 4.6 mm i.d., 5 µm) and Chiralpak AD-RH column (150 mm × 4.6 mm i.d., 5 µm) for temazepan; Methanol-20 mM ammonium acetate aqueous solution (90:10, v/v), 0.1% formic acid (pH 4). | Canada Wastewater effluents from 1 rural aerated lagoon and 2 urban tertiary WWTP (Alberta). | EF = 0.40–0.52; EF = 0.39–0.52; - EF = 0.34–0.41; EF = 0.44–0.62; - - EF = 0.39–0.49. | [103] |
Atenolol Citalopram Fluoxetine Metoprolol Nadolol Pindolol Propranolol Salbutamol Sotalol | LC-MS/MS; Inline filter and a Chirobiotic V (250 mm × 4.6 mm i.d., 5 µm) with a nitrile guard cartridge (10 mm × 3 mm i.d.); Methanol-20 mM ammonium acetate aqueous solution (90:10, v/v), 0.1% formic acid (pH 4). | Canada Raw and treated wastewater from a tertiary WWTP (Alberta). | IWW: 971 ± 30 ng L−1; EWW: 664 ± 22 ng L−1; IWW: 307 ± 18 ng L−1; EWW: 207 ± 11 ng L−1; IWW: 18 ± 2 ng L−1; EWW: 14 ± 0.1 ng L−1; IWW: 411 ± 15 ng L−1; EWW: 375 ± 24 ng L−1; IWW: 51 ± 2 ng L−1; EWW: 20 ± 0.5 ng L−1; IWW: <MQL; EWW: <MQL; IWW: 10 ± 1 ng L−1; EWW: 45 ± 1 ng L−1; IWW: 20 ± 3 ng L−1; EWW: 17 ± 1 ng L−1; IWW: 529 ± 10 ng L−1; EWW: 466 ± 24 ng L−1. | [104] |
Atenolol Metoprolol Propranolol | LC-MS/MS; In-line filter Chirobiotic V (250 mm × 4.6 mm i.d., 5 µm) with a nitrile guard cartridge (10 mm × 3 mm i.d.); Methanol-0.1% TEAA in water (90:10, v/v), acetic acid (pH 4). | Canada Influents and effluents wastewaters from 1 rural aerated lagoon and 2 urban tertiary WWTP (Alberta). | 160–1100 ng L−1; EF ≈ 0.5 (both influent and effluent). 170–520 ng L−1; EF = 0.5 (influent) EF ≠ 0.50 (effluent). 20–92 ng L−1; EF ≈ 0.5 (both influent and effluent). | [84] |
Propranolol | GC-MS after diastereomer formation with the chiral derivatizing reagent α-methoxy-α-(trifluoromethyl)phenylacetic acid; MDN-5S column (30-m, 0.25-mm i.d., 0.25-µm film thickness), carrier gas helium. | USA Surface water Wastewater influent Wastewater effluent after secondary treatment (7 WWTPs in California and New York). | <0.1–32 ng L−1; EF = 0.42–0.53. 13–250 ng L−1; EF = 0.50 ± 0.02. 3–160 ng L−1; EF ≤ 0.42. | [61]. |
Metoprolol | GC-MS after diastereomer formation with the chiral derivatizing reagent (-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid); MDN-5S column (30-m, 0.25-mm i.d., 0.25-µm film thickness), carrier gas helium. | USA River water (Trinity River, Dallas, TX); Effluent wastewater. | 10–571 ng L−1; EF = 0.31–0.44. <1–2269 ng L−1; EF = 0.50 ± 0.03. | [85]. |
Metoprolol | LC-MS/MS; Reprosil AGP column (100 × 2 mm i.d., 5 μm); H2O-acetonitrile (98:2, v/v), containing 10 mM ammonium acetate. | Germany River water (stretch of river Gründlach, Northern Bavaria). | 42–440 ng L−1; EF = 0.43–0.49. | [75] |
Metoprolol and two of its metabolites: α-Hydroxymetoprolol (α-OH-metoprolol) Deaminated metoprolol (COOH-metoprolol) | LC-MS/MS; enantiomers of metoprolol and four stereoisomers of α-OH-metoprolol: in-line high-pressure filter (4 mm, 0.5 µm) and a Chiral-CBH column (100 × 2.0 mm i.d., 5 µm) with a Chiral-CBH guard column; 2% (v/v) methanol in hydroxylamine (5.0 mM)-acetic acid (0.65 mM) buffer at pH 7.0. | Sweden Treated wastewater samples from a municipal WWTP, Uppsala). | (S)-metoprolol: 1140–1860 pM; (R)-metoprolol: 939–1770 pM; EF metoprolol = 0.51–0.55; EF α-OH-metoprolol = 0.13–0.48. | [62] |
LC-MS/MS; enantiomers of COOH-metoprolol: in-line high-pressure filter with a replaceable cap frit (4 mm, 0.5 µm) and a Chiral AGP column (100 mm × 2.0 mm, 5 µm) with a Chiral-AGP guard column (10 × 2.0 mm); Methanol-10 mM ammonium acetate buffer at pH 5.0 (5:95, v/v) | n.d. | |||
Metoprolol and three of its metabolites: α-Hydroxymetoprolol Metoprolol acid O-desmethylmetoprolol | LC-MS/MS; CHIROBIOT V (250 mm × 4.6 mm i.d., 5 µm); Mobile phase not referred. H2O-30 mM ammonium acetate in methanol at pH 6.0 (10:90, v/v). | France Influent and effluent wastewater. | IWW: 0.49–0.52; EWW: 0.57–0.70. | [90] |
Atenolol Metoprolol Pindolol Propranolol | LC-UV; Chiralpak AD-H, Lux Cellulose-1, Sumichiral OA-4900 and Chirobiotic T, (250 × 4.6 mm i.d., 5 µm); n-hexane-ethanol-DEA (70:30:0.3, v/v/v) | Spain River water (Cega River, Segovia). | Not determined; Not determined; Not determined; (S)-propranolol: 1.22 (±0.07) ng L−1; (R)-propranolol: 1.35 (±0.07) ng L−1. | [78] |
Atenolol Metoprolol Pindolol Propranolol | LC-UV; Lux Cellulose-1 (250 × 4.6 mm i.d., 5 µm); Gradient elution mobile phase polarity from n-hexane-Ethanol-DEA (90:10:0.5, v/v/v) to (60:40:0.5, v/v/v) | Spain River water (Cega River, Segovia). | <LOQ; <LOQ; <LOQ; <LOQ. | [79] |
Ibuprofen, and its main metabolites | GC-MS; Homemade OV1701-DMPen (DMPen ) heptakis(2,6-O-dimethyl-3-O-n-pentyl)-â-cyclodextrin; 1:1 diluted with OV1701) fused silica column (16 m, i.d. 0.25 mm) | Switzerland Lake, rivers and sea water (North Sea) Influents wastewaters Effluent wastewaters after secondary treatment. | n.d.—7.8 ng L−1; ER = 0.7–4.2. 990–3300 ng L−1; ER = 5.8–8.0. 2–81 ng L−1; ER 0.9–2. | [60] |
Ibuprofen Naproxen | GC-MS; Astec Chiraldex chiral column (20-m, 0.25-mm i.d., 0.12-µm film thickness) coated with dimethyl-b-cyclodextrin as CSP, carrier gas helium. | Spain Influent and effluent wastewaters from a conventional WWTP from León (Castilla y León, Spain). | IWW EF = 0.73–0.90, EWW EF = 0.60–0.76; IWW EF = 0.88–0.90, EWW EF = 0.71–0.86. | [83] |
Ibuprofen Ketoprofen Naproxen | LC-MS/MS Sumichiral OA-2500 (stationary phase:(R)-1-naphthylglycine and 3.5-dinitrobenzoic acid (250 mm × 46 mm i.d., 5 µm); Tetrahydrofuran-50 mM ammonium acetate in methanol (90:10, v/v). | Spain Influents and effluents wastewaters from 2 WWTPs (Córdoba) | EF IWW: 0.79–0.86; EF EWW: 0.63–0.68; EF IWW: 0.54–0.68; EF EWW: 0.61–0.68; EF IWW: 0.99; EF EWW: 0.93–0.96. | [65] |
Ibuprofen Naproxen | GC-MS after diastereomer formation with the chiral derivatizing reagent (R)-1-phenylethylamine; HP5-MS fused silica capillary column (30 m, 0.25 mm i.d., 0.25 µm film thickness), carrier gas helium. | Australia Influent and effluent wastewater from 3 WWTPs | EF IWW: 0.6–0.8; EF EWW: 0.5. EF IWW: 1.0; EF EWW: 0.7–0.9. | [89] |
Ibuprofen Ketoprofen Naproxen | GC-MS after diastereomer formation with the chiral derivatizing reagent (R)-1-phenylethylamine; HP5-MS fused silica capillary column (30 m, 0.25 mm i.d., 0.25 µm film thickness), carrier gas helium. | Australia Effluent wastewater from a tertiary wastewater treatment plant (Sydney) | 4.6–120 ng L−1; EF = 0.49–0.62; 3.1–207 ng L−1; EF = 0.54–0.66; 1.6–178.9 ng L−1; EF = 0.66–0.86. | [80] |
Ibuprofen Ketoprofen Naproxen | GC-MS after diastereomer formation with the chiral derivatizing reagent (R)-1-phenylethylamine; HP5-MS fused silica capillary column (30 m, 0.25 mm i.d., 0.25 µm film thickness), carrier gas helium. | Australia Effluent wastewater from MBR of a WWTP (Bega Valley) | EF IWW: 0.88–0.94 EF EWW: 0.38–0.40; EF IWW: 0.56–0.60 EF EWW: 0.54–0.68; EF IWW: 0.99 EF EWW: 0.86–0.94. | [67] |
Naproxen 6-O-desmethyl desmethyl-naproxen | LC-MS/MS; Chiralpak AD-RH (150 mm × 4.6 mm i.d.); Acetonitrile-0.1% formic acid (50:50, v/v). | Japan Influent and effluent wastewaters (Tokyo); River water (Tama River basin, Tokyo). | EF IWW: 1.0; EF EWW: 0.88–0.91; RW: 0.84–0.98. | [91] |
Lansoprazole Pantoprazole | LC-MS/MS; Amylose tris-(3,5-dimethoxyphenylcarbamate) (150 mm × 4.6 mm i.d.) coated onto APS-Nucleosil (500 Å, 7 µm, 20%, w/w); Acetonitrile-H2O (35:65, v/v). | Brazil Influent and effluent wastewater; River water (Monjolinho River; São Carlos, SP). | Lansoprazole: n.d.; Pantoprazole: 0.15–0.18 µgL−1 in treated effluents; 0.013 µgL−1 in river water. | [55] |
Omeprazole | LC-MS/MS; LC-UV; Amylose tris-(3,5-dimethylphenylcarbamate) (150 mm × 4.6 mm i.d.) coated onto APS-Nucleosil (500 Å, 7 µm, 20%, w/w); Acetonitrile-H2O (35:65, v/v). | Brazil Influent and effluent wastewater; River water (Monjolinho River; São Carlos, SP). Portugal Estuarine water samples (Douro River). | Both enantiomers were detected in one influent sample (not quantified); Both enantiomers were detected in one estuarine water sample (not quantified). | [54] |
Omeprazole Lnsoprazole Pantoprazole Rabeprazole | LC-MS/MS; LC-UV; Chiralpak IC (250 mm × 4.6 mm i.d., 5 μm) Cellulose tris (3,5-dichlorophenylcarbamate) immobilized on silica; Acetonitrile-5 mM ammonium acetate in water (40:60, v/v) | China Influent and effluent wastewater from a municipal WWTP (Shenyang); River water (riverbank from the South Canal of Shenyang). | IWW: 0.70; EWW: 0.53; RW: 0.54. IWW: 0.51; EWW: 0.52; RW: 0.52. IWW: 0.54; EWW: 0.51; RW: 0.53. IWW: 0.52; EWW: <MQL; RW: 0.51. | [64] |
Venlafaxine | LC-MS/MS; Chirobiotic V column (250 mm × 2.1 mm i.d., 5 µm) with a Chirobiotic guard column (10 mm × 2 mm i.d.); Tetrahydrofuran-8.7 mM ammonium acetate aqueous solution at pH 6.0 (10:90, v/v). | France Wastewater effluent River water | EF = 0.46–0.74. | [72] |
Venlafaxine and its metabolites O-desmethylvenlafaxine, N-desmethylvenlafaxine,O,N-didesmethylvenlafaxine,N,N-didesmethylvenlafaxine and tridesmethylvenlafaxine | LC-MS/MS; CHIROBIOT V (250 mm × 4.6 mm i.d., 5 µm); LC-MS/MS α1-acid glycoprotein column (100 mm × 4.0 mm i.d., 5 µm) | Israel Six wastewater treatment plants (WWTPs) operating under different conditions. | [73] | |
Fluoxetine and norfluoxetine | LC-MS/MS; In-line high-pressure filter with a replaceable cap frit (4 mm, 0.5 µm) and a Chiral AGP column (100 mm × 2.0 mm, 5 µm) with a Chiral-AGP guard column (10 mm × 2.0 mm); Acetonitrile-10 mM ammonium acetate buffer, pH 4.4 (3:97, v/v). | Sweden Influent and effluent wastewater from a municipal WWTP (Uppsala). | IWW: (S)-fluoxetine: 52 pM; (R)-fluoxetine: 21 pM; EF = 0.71; EWW: (S)-fluoxetine: 48 pM; (R)-fluoxetine: 19 pM; EF = 0.71; IWW: (S)-norfluoxetine: 27 pM; (R)-norfluoxetine: 12 pM; EF = 0.69; EWW: (S)-norfluoxetine: 9 pM; (R)-norfluoxetine: 4 pM; EF = 0.68. | [81,100] |
Fluoxetine and norfluoxetine | LC-FD; Chirobiotic V column (150 mm × 4.6 mm i.d., 5 µm); Ethanol-10 mM ammonium acetate buffer (87.5:12.5, v/v), pH 6.8. | Portugal Effluent wastewater from a municipal WWTP. | n.d. | [86] |
Hexaconazole Triadimefon Tebuconazole Penconazole | LC-DAD Chiralpak IC column 250 mm × 4.6 mm i.d., 5 µm). with the CSPs [cellulose tris-(3,5-dichlorophenylcarbamate)] polymer immobilized on silica; n-hexane/2-propanol (90:10, v/v). | Ground water River water | n.d. | [63] |
Econazole Miconazole Tebuconazole Ketoconazole | LC-MS/MS; α1-acid glycoprotein column (100 mm × 4.0 mm i.d., 5 µm); Mobile phase not referred. | China Wastewater (dissolved and suspended particulate matter) sludge and river water (Pearl River Delta) | EF (dissolved phase) = 0.47–0.53; EF (suspended particulate matter) = 0.45–0.53; EF (sludge) 0.47–0.53; EF (river water) = 0.47–0.61. | [88] |
Ketoconazole | LC-MS/MS; HSA column (100 mm × 2 mm i.d., 5.0 μm) with a HSA guard column (10 mm × 2 mm i.d.); Acetonitrile-H2O (10:90, v/v) containing 10 mM ammonium acetate (pH 7.0). | China Influent and effluent wastewater and sludge from a sewage treatment plant (Guangzhou, South China). | IWW: <MQL—91.6 ng L−1; EF = 0.48; EWW: <MQL—12.4 ng L−1; EF = 0.48; Sludge: 230.9–231.9 ng g−1 (dw); EF = 0.49–0.50. | [74] |
Econazole Miconazole Tebuconazole Propiconazole | LC-MS/MS; AGP column (100 mm × 4 mm i.d., 5.0 μm) with an AGP guard column (10 mm × 4 mm i.d.); Gradient of H2O containing 10 mM ammonium acetate (pH 7.0) and acetonitrile. | IWW: 1–1.2 ng L−1; EF not determined; EWW: 0.29–0.51 ng L−1; EF not determined; Sludge: 8.3–120.8 ng g−1 (dw); EF = 0.50–0.51; IWW: 6.0–11.3 ng L−1; EF = 0.50; EWW: 0.25–0.87 ng L−1; EF = 0.47; Sludge: 87.9–1258.0 ng g−1 (dw); EF = 0.49–0.50. n.d.; n.d. |
Pesticides | Chiral Compound | Analytical Method | Location/Matrix | Concentration/ER, EF | Ref. |
α-HCH | GC-ECD heptakis (3-O-butyryl-2,6-di-O-pentyl)-β-CD (60 m), carrier gas hydrogen | North Sea regions | α-HCH: 0.54–2.86 ng L−1 ER (+/-, α-HCH)= 0.88–1.19 γ-HCH: 0.31–2.72 ng L−1 | [97] | |
α-HCH | GC-ECD β-dex 120 chiral column | USA York river estuary | (+) α-HCH: 11.6–79.3 pg L−1 (-) α-HCH: 20.6–103.0 pg L−1 ER (+/-, α-HCH) = 0.71–1.06 | [114] | |
α-HCH | GC-ECD γ-DEX 120 column (20%-γ-CD, 20 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas hydrogen | Island Water rivers and lakes | α-HCH: 1.2–5.8 ng L−1 γ-HCH: 0.23–0.65 ng L−1 ER (α/γ, HCH) = 3.5–13.8 | [142] | |
α-HCH | GC-ECD column A: heptakis (3-O-butyryl-2,6-di-O-pentyl)-β-CD (25 m, i.d. 0.25 mm); column B: 50% heptakis (2,3,6-tri-O-n-pentyl)-β-CD and 50% OV1701(25 m, i.d. 0.25 mm), carrier gas helium | North sea and Baltic sea | γ-HCH: 2.0–7.7 ng L−1 α-HCH: 0.2–5.8 ng L−1 ER (γ/α, HCH) = 0.67–10.0 ER (+/-, α-HCH) = 0.81–0.92 | [99] | |
α-HCH | GC-MS 30% tert-butyldimethylsilylated-β-CD in PS-086 (20 m, i.d. 0.25 mm, 0.25 µm film thickness) | Arctic regions water from Bering and Chukchi Seas | α-HCH: 0.05–5.32 ng L−1 γ-HCH: 0.10–1.33 ng L−1 ER (α/γ, HCH) = 0.35–12.40 | [121] | |
α-HCH | GC-MS Beta-DEX (20% permethylated-β-CD in polydimethylsiloxane, (30 m, i.d. 0.25 mm, 0.25 µm film thickness) and BGB-172 (20% tert-butyldimethylsilylated-β-CD in OV-1701, (30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | Arctic Ocean Surface water | ER (+/-,α-HCH) = 0.68–1.09 | [143] | |
α-HCH | GC-MS Betadex-120 (20% permethylated β-CD in methyl phenylpolysiloxane (30 m, i.d. 0.25 mm) | Canada Lake Ontario and Niagara River Rain water | ER (+/-, α-HCH) = 0.86 ER (+/-, α-HCH) = 0.99 | [112] | |
α-HCH | Not described | Scotland Kintyre Peninsula Air | EF (α-HCH) = 0.480 | [144] | |
α-HCH | GC-MS 20% tert-butyldimethylsilylated β-cyclodextrin in OV-1701 | China Pearl River Delta | EF(α-HCH) = 0.104–0.910 | [12] | |
α-HCH | GC-MS BGB (20% tert-butyldimethylsilylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF(α-HCH) = 0.48–0.53 EF(α-HCH) = 0.50 | [113] | |
PCCH | GC-ECD column A: heptakis (3-O-butyryl-2,6-di-O-pentyl)-β-CD (25 m, i.d. 0.25 mm); column B: 50% heptakis (2,3,6-tri-O-n- pentyl)-β-CD and 50% OV1701(25 m, i.d. 0.25 mm), carrier gas helium | North sea and Baltic sea | ER (γ1/γ2) PCCH = 1.12–1.17 ER (β1/β2) PCCH = 0.97 | [99] | |
bromocyclin | GC-ECD 50% heptakis(6-O-tert-butyl-dimethylsilyl-2,3-di-O-methyt)-β-CD and 50% OV-I7O1 ~w/w (25 m, i.d. 0.25 mm, 0.125 µm film thickness) carrier gas hydrogen | Germany River Stör WWTPs | n.d.–261 pg L−1; ER (-/+) = 1.01–1.0 760–11,500 pg L−1 | [126] | |
MCPP | GC-MS FS 71 PS-086 + 20% Me-β-CD, (15 m, 0.25 mm i.d., 0.13 µm film thickness) | Switzerland Rain water | R-MCPP: up to 50 ng L−1 S-MCPP: up to 19 ng L−1 | [115] | |
MCPP | GC-MS OV1701-TBDM (TBDM, heptakis-(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-CD) fused silica (20 m, i.d. 0.25 mm) column with 35% of the chiral selector (amount relative to OV1701) | Switzerland Lake and rivers | R-MCPP: <0.2 to 25 ng L−1 S-MCPP: <0.2 to 121 ng L−1 ER (R/S) = 0.21–4.36 | [124] | |
MCPP | GC-MS Not described | Switzerland WWTPs and Lake Greifensee | ER (R/S )= ~1 to 2 | [125] | |
DCPP | GC-MS FS 71 PS-086 + 20% Me-β-CD, (15 m, 0.25 mm i.d., 0.13 µm film thickness) | Switzerland Rain water | R-dichlorprop: up to 106 ng L−1 S-dichlorprop: up to 11 ng L−1 | [115] | |
DCPP | GC-MS OV1701-TBDM (TBDM, heptakis-(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-CD) fused silica (20 m, i.d. 0.25 mm) column with 35% of the chiral selector (amount relative to OV1701) | Switzerland Lake and rivers | R-DCPP: <0.2 to 2.7 ng L−1 S-DCPP: <0.2 to 2.7 ng L−1 | [124] | |
TC | GC-MS BGB-172 (20% tert-butyldimethylsilylated-β-CD in OV-1701, (30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | Arctic Ocean Surface water | ER (+/- TC): 0.97–1.03 | [143] | |
TC | Not described | Scotland Kintyre Peninsula Air | EF (TC) = 0.476 | [144] | |
TC | GC-MS 20% tert-butyldimethylsilylated β-cyclodextrin in OV-1701 | China Pearl River Delta | EF (TC) = 0.112–0.734 | [12] | |
TC | GC-MS Betadex (20% permethylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (TC) = 0.47–0.49 EF (TC) = 0.40–0.50 | [113] | |
CC | GC-MS BGB-172 (20% tert-butyldimethylsilylated-β-CD in OV-1701, (30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | Arctic Ocean Surface water | ER (+/- CC) = 0.94–1.06 | [143] | |
CC | Not described | Scotland Kintyre Peninsula Air | EF (CC) = 0.511 | [144] | |
CC | GC-MS 20% tert-butyldimethylsilylated β-cyclodextrin in OV-1701 | China Pearl River Delta | EF (CC) = 0.043–0.813 | [12] | |
CC | GC-MS Betadex (20% permethylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (CC) = 0.50–0.56 EF (CC) = 0.48–0.53 | [113] | |
OXY | GC-MS BGB (20% tert-butyldimethylsilylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (OXY) = 0.55–0.60 EF (OXY) = 0.550 | [113] | |
HEPX | GC-MS BGB (20% tert-butyldimethylsilylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (HEPX) = 0.69–0.73 EF (HEPX) = 0.50–0.76 | [113] | |
MC5 | GC-MS Betadex (20% permethylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (MC5) = 0.25–0.46 EF (MC5) = 0.41–0.47 | [113] | |
DDT | GC-MS 20% tert-butyldimethylsilylated β-cyclodextrin in OV-1701 | China Pearl River Delta | EF (o,p’-DDT) = 0.102–0.801 | [12] | |
DDT | GC-MS BGB (20% tert-butyldimethylsilylated β-CD, 30 m, i.d. 0.25 mm, 0.25 µm film thickness), carrier gas helium | USA Alabama Agricultural soil Cemeteries | EF (o,p’-DDT) = 0.41–0.55 EF (o,p’-DDT) = 0.50–0.57 | [113] | |
PBs | PCB 91 | GC-ECD and GC-MS Chirasil-Dex | USA Lake Hartwell sediment | ER (first/second enantiomer) = 0.56 | [110] |
PCBs 95, 132, and 149 | GC-ECD Chirasil-Dex (10 m, i.d. 0.25 mm, 0.2 µm film thickness), carrier gas hydrogen | Germany River Elsenz | ER (PCBs 95, 132, and 149) ~ 1 | [138] | |
PCB 95 | GC-ECD Chirasil-Dex CB (25 m, i.d. 0.25 mm 0.25 µm film thickness), carrier gas hydrogen | USA Sediments Hudson River in New York State | ER = 0.5–0.6 | [137] | |
PCBs 91, 95, 132, 136, 149, 174, and 176 | GC-MS Chirasil-Dex Cyclosil-B | USA Sediments Hudson and Housatonic Rivers | ER (E1/E2, PCB 91) = 0.56–1.28 ER (E1/E2, PCB 95) = 0.67–1.02 ER (+/-, PCB 132) = n.d.–1.32 ER (+/-, PCB 136) = n.d.–5.33 ER (+/-, PCB 149) = 0.91–2.31 ER (+/-, PCB 174) = n.d.–3.71 ER (+/-, PCB 176) = n.d.–1.02 ER (+/-, PCB 183) = n.d.–1.04 | [10] | |
PCBs 95, 136, 149 | GC-MS Chirasil-Dex (10% permethylated 2,3,6-tri-O-methyl-β-CD (25 m × 0.25 mm × 0.25 µm film thickness) | U.K West Midlands Air Soil | EF (95) = 0.488–0.499 EF (136) = 0.495–0.503 EF (149) = 0.495–0.500 EF (95) = 0.444–0.496 EF (136) = 0.472–0.522 EF (149) = 0.490–0.544 | [145] | |
Polycyclic musk | HHCB | GC-MS/MS Cyclosil-B: heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl-β-CD in DV-1701 (25 m, i.d.0.25 mm, 0.25 µm film thickness), carrier gas helium | Korea Nakdong River WWTPs Influent Effluent | <18.0–342.0 ng L−1; ER (trans-HHCB) = 0.86–1.09 ER (cis-HHCB) = 0.95–1.10 <785.0–3491 ng L−1; ER (trans-HHCB) = 0.91–1.01 ER (cis-HHCB) = 1.03–1.14 <284.0–576.0 ng L−1; ER (trans-HHCB) = 0.74–1.04 ER (cis-HHCB) = 0.69–1.25 | [139] |
HHCB | GC-MS/MS 14% cyanopropylphenyl/86% dimethyl polysiloxane) doped with proprietary amounts of cyclodextrin material (30 m, i.d. 0.25 mm, 0.25 µm film thickness) OV 1701 capillary column, carrier gas helium | Switzerland WWTPs Influent Effluent Sewage sludge Aerobic Anaerobic | ER (trans-HHCB) = 1.0 ER (cis-HHCB) = 0.97 ER (trans-HHCB) = 0.81 ER (cis-HHCB) = 1.00 ER (trans-HHCB) = 0.93 ER (cis-HHCB) = 0.98 | [140] | |
HHCB | GC-MS; Chiral heptakis (2,3-di-O-methyl-6-O-t-butyl dimethylsilyl)-a-cyclodextrin column combined with a (non-chiral) HP-5MS column. | Effluent wastewater biologically treated; Advanced treated recycled water. | 1679 ng L−1; EF = 0.25/0.25/0.26; 28.1 ng L−1; EF = 0.24/0.24/0.25; | [70] | |
AHTN | GC-MS/MS 14% cyanopropylphenyl/86% dimethyl polysiloxane) doped with proprietary amounts of cyclodextrin material (30 m, i.d. 0.25 mm, 0.25 µm film thickness) OV 1701 capillary column, carrier gas helium | Switzerland WWTPs Influent Effluent Sewage sludge Aerobic Anaerobic | ER = 0.94 ER = 0.96 ER = 1.17 ER = 0.99 | [140] | |
AHTN | GC-MS; Chiral heptakis (2,3-di-O-methyl-6-O-t-butyl dimethylsilyl)-a-cyclodextrin column combined with a (non-chiral) HP-5MS column. | Effluent wastewater biologically treated; Advanced treated recycled water. | 31.2 ng L−1; EF = 0.50; 4.6 ng L−1; EF = 0.50; | [70] | |
AHDI | GC-MS/MS Cyclosil-B: heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl-β-CD in DV-1701 (25 m, i.d.0.25 mm, 0.25 µm film thickness), carrier gas helium | Korea Nakdong River WWTPs Influent Effluent | <69.0 ng L−1 <69.0 ng L−1 | [139] | |
AHDI | GC-MS/MS 14% cyanopropylphenyl/86% dimethyl polysiloxane) doped with proprietary amounts of CD material (30 m, i.d. 0.25 mm, 0.25 µm film thickness) OV 1701 capillary column, carrier gas helium | Switzerland WWTPs Influent Effluent Sewage sludge Aerobic Anaerobic | ER = 0.97 ER = 1.19 ER = 1.16 ER = 0.95 | [140] | |
ATII | GC-MS/MS Cyclosil-B: heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl-β-CD in DV-1701 (25 m, i.d.0.25 mm, 0.25 µm film thickness), carrier gas helium | Korea Nakdong River WWTPs Influent Effluent | <107.0 ng L−1 <107.0 ng L−1 | [139] | |
ATII | GC-MS/MS 14% cyanopropylphenyl/86% dimethyl polysiloxane) doped with proprietary amounts of CD material (30 m, i.d. 0.25 mm, 0.25 µm film) OV 1701 capillary column, carrier gas helium | Switzerland WWTPs Influent Effluent Sewage sludge Aerobic Anaerobic | ER = 0.86 ER = 2.94 ER = 0.92 ER = 0.79 | [140] | |
ATII | GC-MS; Chiral heptakis (2,3-di-O-methyl-6-O-t-butyl dimethylsilyl)-a-cyclodextrin column combined with a (non-chiral) HP-5MS column. | Effluent wastewater biologically treated; Advanced treated recycled water. | 5.0 ng L−1; EF = 0.55; n.d. | [70] | |
DPMI | GC-MS/MS Cyclosil-B: heptakis (2,3-di-O-methyl-6-O-tert-butyldimethylsilyl-β-CD in DV-1701 (25 m, i.d.0.25 mm, 0.25 µm film thickness), carrier gas helium | Korea Nakdong River WWTPs Influent Effluent | <79.0 ng L−1 <79.0 ng L−1 | [139] | |
DPMI | GC-MS; Chiral heptakis (2,3-di-O-methyl-6-O-t-butyl dimethylsilyl)-a-cyclodextrin column combined with a (non-chiral) HP-5MS column. | Effluent wastewater biologically treated; Advanced treated recycled water. | 66.6 ng L−1; EF = 0.48. 2.2 ng L−1; EF = 0.51. | [70] |
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Ribeiro, C.; Ribeiro, A.R.; Maia, A.S.; Tiritan, M.E. Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review. Symmetry 2017, 9, 215. https://doi.org/10.3390/sym9100215
Ribeiro C, Ribeiro AR, Maia AS, Tiritan ME. Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review. Symmetry. 2017; 9(10):215. https://doi.org/10.3390/sym9100215
Chicago/Turabian StyleRibeiro, Cláudia, Ana Rita Ribeiro, Alexandra S. Maia, and Maria Elizabeth Tiritan. 2017. "Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review" Symmetry 9, no. 10: 215. https://doi.org/10.3390/sym9100215