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Chiral Xenobiotics in the Environment

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Chiral Environmental Pollutants

Abstract

The authors of the present monograph would like to leave it to the reader’s judgment as to whether the rapid development of the enantioselective analytical approaches and the results that have thus become accessible during the last decade, as summarised in the subsequent chapters, still justify the critical remarks cited above.

Neglect of stereoselectivity of biological objects and stereospecifity of bioactive agents nevertheless is a still persisting aspect of today’s pharmacology and toxicology. It results in heavily biased “scientific” data such as half-life times, biological availabilities, concentration response relationships etc. for racemates and mixtures of isomers in general. It is like presenting the age or body weight of a married couple or even a four-person family (a mixture of 4 stereoisomers) in one figure. Such impressive nonsense is still rather common.

Ariëns, 1988 [150]

In the case of chiral pollutants, environmental studies have historically neglected to determine the adverse effects associated with particular enantiomers, and which enantiomers may persist in the environment. Consequently, much of the environmental data that has been collected for chiral pollutants, including many of the chemicals raising the greatest public concern, may have represented only the presence of relatively innocuous enantiomers.

Lewis et al., Oct. 1999 [164]

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References

  1. Ludwig P, Hühnerfuss H, König WA, Gunkel W (1992) Gas chromatographic separation of the enantiomers of marine pollutants. 3. Enantioselective degradation of ahexachlorocyclohexane by marine microorganisms. Mar Chem 38: 13–23

    Article  CAS  Google Scholar 

  2. Hühnerfuss H, Faller J, König WA, Ludwig P (1992) Gas chromatographic separation of the enantiomers of marine pollutants. 4. Fate of hexachlorocyclohexane isomers in the Baltic and North Sea. Environ Sci Technol 26: 2127–2133

    Google Scholar 

  3. Cristol JS (1949) The structure of a-benzene hexachloride. J Am Chem Soc 71: 1894

    Article  CAS  Google Scholar 

  4. Vetter W, Klobes U, Luckas B, Hottinger G (1998) Determination of (+/-) elution orders of chiral organochlorines by liquid chromatography with a chiral detector and by enantioselective gas chromatography. J AOAC Int 81: 1245–1251

    Google Scholar 

  5. Ludwig P (1991) Untersuchungen zum enantioselektiven Abbau von polaren and un-polaren chlorierten Kohlenwasserstoffen durch marine Mikroorganismen. PhD thesis, University of Hamburg, Germany

    Google Scholar 

  6. Ludwig P, Gunkel W, Hühnerfuss H (1992) Chromatographic separation of the enantiomers of marine pollutants. 5. Enantioselective degradation of phenoxycarboxylic acid herbicides by marine microorganisms. Chemosphere 24: 1423–1429

    Google Scholar 

  7. Buser H-R, Müller MD (1995) Isomer and enantioselective degradation of hexachlorocyclohexane isomers in sewage sludge under anaerobic conditions. Environ Sci Technol 29: 664–672

    Article  CAS  Google Scholar 

  8. Faller J, Hühnerfuss H, König WA, Krebber R, Ludwig P (1991) Do marine bacteria degrade a-hexachlorocyclohexane stereoselectively? Environ Sci Technol 25: 676–678

    Article  CAS  Google Scholar 

  9. Faller J, Hühnerfuss H, König WA, Ludwig P (1991) Gas chromatographic separation of the enantiomers of marine organic pollutants. Distribution of a-HCH enantiomers in the North Sea. Mar Pollut Bull 22: 82–86

    Google Scholar 

  10. Gaul H, Ziebarth U (1983) Methods for the analysis of lipophilic components in water and results about the distribution of different organochlorine components in the North Sea. Dt Hydrogr Z 36: 191–212

    Article  Google Scholar 

  11. Falconer RL, Bidleman TF, Gregor DJ, Semkin R, Teixeira C (1995) Enantioselective breakdown of a-hexachlorcyclohexane in a small arctic lake and its watershed. Environ Sci Technol 29: 1297–1302

    Article  CAS  Google Scholar 

  12. Falconer RL, Bidleman TF, Gregor DJ (1995) Air-water gas exchange and evidence for metabolism of hexachlorocyclohexanes in Resolute Bay,N.W.T. Sci Total Environ 160 /161: 65–74

    Article  Google Scholar 

  13. Ridal JJ, Bidleman TF, Kerman BR, Fox ME, Strachan WMJ (1997) Enantiomers of ahexachlorocyclohexanes as tracers of air-water gas exchange in Lake Ontario. Environ Sci Technol 31: 1940–1945

    Article  CAS  Google Scholar 

  14. Bidleman TF, Jantunen LM, Harner T, Wiberg K, Wideman JL, Brice K, Su K, Falconer RL, Aigner EJ, Leone AD, Ridal JJ, Kerman B, Finizio A, Alegria H, Parkhurst WJ, Szeto SY (1998) Chiral pesticides as tracers of air-surface exchange. Environ Pollut 101: 1–7

    Article  Google Scholar 

  15. Jantunen LM, Bidleman T (1996) Air-water gas exchange of hexachlorocyclohexanes (HCHs) and the enantiomers of a-HCH in arctic regions. J Geophys Res 101:28,83728,846; Correction: (1997) J Geophys Res 102:19, 279–19, 282

    Google Scholar 

  16. Jantunen LMM, Bidleman TF (1998) Organochlorine pesticides and enantiomers of chiral pesticides in Arctic ocean water. Arch Environ Contam Toxicol 35: 218–228

    Article  CAS  Google Scholar 

  17. Kallenborn R, Hühnerfuss H, König WA (1991) Enantioselective metabolism of (±)-ahexachlorocyclohexane in organs of the Eider duck. Angew Chem 103:328–329; Angew Chem Int Ed Engl 30: 320–321

    Article  Google Scholar 

  18. Hühnerfuss H, Kallenborn R (1992) Review. Chromatographic separation of marine organic pollutants. J Chromatogr 580: 191–214

    Google Scholar 

  19. Möller K, Bretzke C, Hühnerfuss H, Kallenborn R, Kinkel JN, Kopf J, Rimkus G (1994) The absolute configuration of (+)-a-1,2,3,4,5,6-hexachlorocyclohexane and its permeation through the seal blood-brain barrier. Angew Chem 106:911–912; Angew Chem Int Ed Engl 33: 882–884

    Article  Google Scholar 

  20. Hardt IH, Wolf C, Gehrcke B, Hochmuth DH, Pfaffenberger B, Hühnerfuss H, König WA (1994) Gas chromatographic enantiomer separation of agrochemicals and polychlorinated biphenyls ( PCBs) using modified cyclodextrins. J High Resolut Chromatogr 17: 859–864

    Google Scholar 

  21. Mössner S, Ballschmiter K (1994) Separations of a-hexachlorocyclohexane (a-HCH) and pentachlorocyclohexene (PCCH) enantiomers on a cyclodextrin-phase ( Cyclodex-B) by HRGC/ECD. Fresenius J Anal Chem 348: 583–589

    Google Scholar 

  22. Koske G, Leupold G, Parlar H (1997) Gas chromatographic enantiomer separation of some selected polycyclic xenobiotics using modified cyclodextrins. Fresenius Envir Bull 6: 489–493

    CAS  Google Scholar 

  23. König WA, Icheln D, Runge T, Pfaffenberger B, Ludwig P, Hühnerfuss H (1991) Gas chromatographic enantiomer separation of agrochemicals using modified cyclodextrins. J High Resolut Chromatogr 14: 530–536

    Article  Google Scholar 

  24. Buser H-R, Müller MD (1992) Enantiomer separation of chlordane components and metabolites using chiral high-resolution gas chromatography and detection by mass spectrometric techniques. Anal Chem 64: 3168–3175

    Article  CAS  Google Scholar 

  25. König WA, Hardt IH, Gehrcke B, Hochmuth DH, Hühnerfuss H, Pfaffenberger B, Rimkus G (1994) Optisch aktive Referenzsubstanzen für die Umweltanalytik. Angew Chem 106:2175–2177; Angew Chem Int Ed Engl 33: 2085–2087

    Article  Google Scholar 

  26. Oehme M, Kallenborn R, Wiberg K, Rappe C (1994) Simultaneous enantioselective separation of chlordanes, a nonachlor compound, and o,p’-DDT in environmental samples using tandem capillary columns. J High Resolut Chromatogr 17: 583–588

    Article  CAS  Google Scholar 

  27. Vetter W, Klobes U, Luckas B, Hottinger G (1997) Enantiomeric resolution of persistent compounds of technical toxaphene ( CTTs) on t-butyldimethylsilylated ß-cyclodextrin phases. Chromatographia 45: 255–262

    Google Scholar 

  28. Karlsson H, Oehme M, Müller L (1996) Enantioselective separation of toxaphene congeners. Results, problems, and challenges. Organohalogen Compd 28: 405–409

    Google Scholar 

  29. König WA, Gehrcke B, Runge T, Wolf C (1993) Gas chromatographic separation of atropisomeric alkylated and polychlorinated biphenyls using modified cyclodextrins. J High Resolut Chromatogr 16: 376–378

    Article  Google Scholar 

  30. Vetter W, Klobes U, Luckas B, Hottinger G (1997) Enantiomer separation of selected polychlorinated biphenyls including PCB 144 on tert-butyldimethylsilylated ß-cyclodextrin. J Chromatogr A 769: 247–252.

    Article  CAS  Google Scholar 

  31. Schurig V, Glausch A (1993) Enantiomer separation of atropisomeric polychlorinated biphenyls ( PCBs) by gas chromatography on Chirasil-Dex. Naturwissenschaften 80: 468–469

    Google Scholar 

  32. Vetter W, Klobes U, Hummert K, Luckas B (1997) Gas chromatographic separation of chiral organochlorines on modified cyclodextrin phases and results in marine biota. J High Resolut Chromatogr 20: 85–93

    Article  CAS  Google Scholar 

  33. Müller MD, Buser H-R, Rappe C (1997) Enantioselective determination of various chlordane components and metabolites using high-resolution gas chromatography with a ß-cyclodextrin derivative as chiral selector and electron-capture negative ion mass spectrometry detection. Chemosphere 34: 2407–2417

    Article  Google Scholar 

  34. Haglund P, Wiberg K (1996) Determination of the gas chromatographic elution sequences of the (+)- and (-)-enantiomers of stable atropisomeric PCBs on ChirasilDex. J High Resolut Chromatogr 19: 373–376

    Google Scholar 

  35. Ellerichmann T, Bergman A, Franke S, Hühnerfuss H, Jakobsson E, König WA, Larsson C (1998) Gas chromatographic enantiomer separation of chiral PCB methyl sulfones and identification of selectively retained enantiomers in human liver. Fresenius Envir Bull 7: 244–257

    CAS  Google Scholar 

  36. Bergman A, Ellerichmann T, Franke S, Hühnerfuss H, Jakobsson E, König WA, Larsson C (1998) Gas chromatographic enantiomer separations of chiral PCB methyl sulfones and identification of selectively retained enantiomers in human liver. Organohalogen Compd 35: 339–342

    CAS  Google Scholar 

  37. Gatermann R, Biselli S, Hühnerfuss H, Rimkus GG, Franke S, Hecker M, Kallenborn R, Karbe L, König WA (2001) Synthetic musks in the environment. 2. Enantioselective transformation of HHCB (Galaxolide®),AHTN (Tonalide®), AHDI (Phantolide®), and ATII (Traseolide®) in freshwater fish. Submitted for publication

    Google Scholar 

  38. Pfaffenberger B, Hühnerfuss H, Kallenborn R, Köhler-Günther A, König WA, Krüner G (1992) Chromatographic separation of the enantiomers of marine pollutants. 6. Comparison of the enantioselective degradation of a-hexachlorocyclohexane in marine biota and water. Chemosphere 25: 719–725

    Google Scholar 

  39. Hühnerfuss H, Faller J, Kallenborn R, König WA, Ludwig P, Pfaffenberger B, Oehme M, Rimkus G (1993) Enantioselective and nonenantioselective degradation of organic pollutants in the marine ecosystem. Chirality 5: 393–399

    Article  Google Scholar 

  40. Hühnerfuss H, Kallenborn R, König WA, Rimkus G (1992) Preferential enrichment of the (+)-a-hexachlorocyclohexane enantiomers in cerebral matter of harbour seals. Organohalogen Compd 10: 97–100

    Google Scholar 

  41. Mössner S, Spraker TR, Becker PR, Ballschmiter K (1992) Ratios of enantiomers of aHCH and determination of a-, ß-, and y-HCH isomers in brain and other tissues of neonatal northern fur seals (Callorhinus ursinus).Chemosphere 24: 1171–1180

    Google Scholar 

  42. Müller MD, Schlabach M, Oehme M (1992) Fast and precise determination of a-hexachlorocyclohexane enantiomers in environmental samples using chiral high-resolution gas chromatography. Environ Sci Technol 26: 566–569

    Article  Google Scholar 

  43. Pfaffenberger B, Hardt I, Hühnerfuss H, König WA, Rimkus G, Glausch A, Schurig V, Hahn J (1994) Enantioselective degradation of a-hexachlorocyclohexane and cyclodiene insecticides in roe-deer liver samples from different regions of Germany. Chemosphere 29: 1543–1554

    Article  CAS  Google Scholar 

  44. Möller K, Hühnerfuss H, Rimkus G (1993) On the diversity of enzymatic degradation pathways of a-hexachlorocyclohexane as determined by chiral gas chromatography. J High Resolut Chromatogr 16: 672–673

    Article  Google Scholar 

  45. Buser H-R, Müller MD, Rappe C (1992) Enantioselective determination of chlordane components using chiral high-resolution gas chromatography-mass spectrometry with application to environmental samples. Environ Sci Technol 26: 1533–1540

    Article  CAS  Google Scholar 

  46. Wiberg K, Oehme M, Haglund P, Karlsson H, Olsson M, Rappe C (1998) Enantioselective analysis of organochlorine pesticides in herring and seal from the Swedish marine environment. Mar Pollut Bull, 36: 345–353.

    Article  CAS  Google Scholar 

  47. Buser H-R, Müller MD (1993) Enantioselective determination of chlordane components, metabolites, and photoconversion products in environmental samples using chiral high-resolution gas chromatography and mass spectrometry. Environ Sci Technol 27: 1211–1220

    Article  CAS  Google Scholar 

  48. Zhu J, Norstrom RJ, Muir DCG, Ferron LA, Weber J-P, Dewailly E (1995) Persistent chlorinated cyclodiene compounds in ringed seal blubber, polar bear fat, and human plasma from northern Québec, Canada: identification and concentrations of photo-heptachlor. Environ Sci Technol 29: 267–271

    Article  CAS  Google Scholar 

  49. Bethan B, Bester K, Hühnerfuss H, Rimkus G (1997) Bromocyclen contamination of surface water, waste water and fish from northern Germany, and gas chromatographic chiral separation. Chemosphere 34: 2271–2280

    Article  CAS  Google Scholar 

  50. Pfaffenberger B, Hühnerfuss H, Gehrcke B, Hardt I, König WA, Rimkus G (1994) Gas chromatographic separation of the enantiomers of bromocyclen in fish samples. Chemosphere 29: 1385–1391

    Article  CAS  Google Scholar 

  51. Buser H-R, Muller MD (1994) Isomer-and enantiomer-selective analyses of toxaphene components using chiral high-resolution gas chromatography and detection by mass spectrometry/mass spectrometry. Environ Sci Technol 28: 119–128

    Article  CAS  Google Scholar 

  52. Hühnerfuss H, Pfaffenberger B, Gehrcke B, Karbe L, König WA, Landgraff 0 (1995) Stereochemical effects of PCBs in the marine environment: seasonal variation of coplanar and atropisomeric PCBs in blue mussels (Mytilus edulis L.) of the German Bight. Mar Pollut Bull 30: 332–340

    Google Scholar 

  53. Glausch A, Nicholson GJ, Fluck M, Schurig V (1994) Separation of the enantiomers of stable atropisomeric polychlorinated biphenyls ( PCBs) by multidimensional gas chromatography on Chirasil-Dex. J High Resolut Chromatogr 17: 347–349

    Google Scholar 

  54. Glausch A, Hahn J, Schurig V (1995) Enantioselective determination of chiral 2,2’,3,3’,4,6’-hexachlorobiphenyl (PCB 132) in human milk samples by multidimensional gas chromatography/electron capture detection and by mass spectrometry. Chemosphere 30: 2079–2085

    Article  CAS  Google Scholar 

  55. Buser H-R, Müller MD, Theobald N (1998) Occurrence of the pharmaceutical drug clofibric acid and the herbicide mecoprop in various Swiss lakes and in the North Sea. Environ Sci Technol 32: 188–192

    Article  CAS  Google Scholar 

  56. Wiberg K, Letcher R, Sandau C, Norstrom R, Tysklind M, Bidleman T (1998) Enantioselective analysis of organochlorines in the Arctic marine food chain: chiral biomagnification factors and relationships of enantiomeric ratios, chemical residues and biological data. Organohalogen Compd 35: 371–374

    CAS  Google Scholar 

  57. Koske G, Leupold G, Angerhöfer D, Parlar H (1998) Multidimensional gas chromatographic enantiomer quantification of some polycyclic xenobiotics in cod liver and fish oils. Organohalogen Compd 35: 363–366

    CAS  Google Scholar 

  58. Jantunen LM, Kylin H, Bidleman TF (1998) Air-water gas exchange of hexachlorocyclohexanes and the enantiomeric ratios of a-HCH in the South Atlantic Ocean and Antarctica. Organohalogen Compd 35: 347–350

    CAS  Google Scholar 

  59. Harner T, Kylin H, Bidleman TF, Strachan WMJ (1998) Air-water gas exchange of hexachlorocyclohexanes ( HCHs) and the enantiomers of a-HCH in the Eastern Arctic Ocean. Organohalogen Compd 35: 355–358

    Google Scholar 

  60. Franke S, Meyer C, Specht M, König WA, Francke W (1998) Chloro-bis-propyl ethers in the Elbe river–isomeric distribution and enantioselective degradation.] High Resolut Chromatogr 21: 113–120

    CAS  Google Scholar 

  61. Miyazaki T, Yamagishi T, Matsumoto M (1985) Isolation and structure of some components in technical grade chlordane. Arch Environ Contam Toxicol 14: 475483

    Google Scholar 

  62. Dearth MA, Hites RA (1991) Complete analysis of technical chlordane using negative-ionization mass spectrometry. Environ Sci Technol 25: 245–254

    Article  CAS  Google Scholar 

  63. Fleming I (1988) Grenzorbitale and Reaktionen organischer Verbindungen. VCH Verlagsgesellschaft, Weinheim, Germany

    Google Scholar 

  64. Hühnerfuss H, Pfaffenberger B, Rimkus G (1996) Enantioselective transformation and accumulation of cyclodiene pesticides at different trophic levels of marine and terrestrial biota. Organohalogen Compd 29: 88–93

    Google Scholar 

  65. Karlsson H, Oehme M, Burkow IC, Evenseth A (1997) Determination of enantiomer ratios of chlordane congeners in cod tissues by HRGC/NICI-MS. Technical problems and influence of biological parameters. Organohalogen Compd 31: 250–253

    Google Scholar 

  66. Bethan B, Bester K, Hühnerfuss H, Rimkus G (1996) Contamination and gas chromatographic chiral separation of bromocyclen in water and fish samples from the River Stör in the northern part of Germany and in some sewage plants’ waste water. Organohalogen Compd 28: 437–440

    CAS  Google Scholar 

  67. Arnold SF, Klotz DM, Collins BM, Vonier PM, Guillette LJ Jr, McLachlan JA (1996) Synergistic activation of estrogen receptor with combinations of environmental chemicals. Science 272: 1489–1492

    Article  CAS  Google Scholar 

  68. Garrison AW, Nzengung VA, Avants JK, Ellington J, Wolfe NL (1997) Determining the environmental enantioselectivity of o,p’-DDT and o,p’-DDD. Organohalogen Compd 31: 256–261

    CAS  Google Scholar 

  69. Bidleman TF, Jantunen LM, Falconer RL, Aigner E, Finizio A, Szeto SY, Ridal JJ (1996) ACS Div of Environmental Chem, Preprints of Extended Abstracts 36: 243–245.

    Google Scholar 

  70. Kallenborn R, Oehme M, Vetter W, Parlar H (1994) Enantiomer selective separation of toxaphene congeners isolated from seal blubber and obtained by synthesis. Chemosphere 28: 89–98

    Article  CAS  Google Scholar 

  71. Buser H-R, Müller MD (1994) Isomeric and enantiomeric composition of different commercial toxaphenes and of chlorination products (+)- and (-)-camphenes. J Agric Food Chem 42: 393–400

    Article  CAS  Google Scholar 

  72. Alder L, Palavinskas R, Andrews P (1996) Enantioselective determination of toxaphene components in fish, monkey adipose tissue from a feeding study and human milk. Organohalogen Compd 28: 410–415

    CAS  Google Scholar 

  73. Vetter W, Klobes U, Luckas B, Hottinger G (1997) Enantioselective determination of toxaphene and other organochlorines on tert-butyldimethylsilylated ß-cyclodextrin. Organohalogen Compd 33: 63–67

    CAS  Google Scholar 

  74. Vetter W, Schurig V (1997) Enantioselective determination of chiral organochlorine compounds in biota by gas chromatography on modified cyclodextrins. J Chromatogr A774: 143–175

    Article  CAS  Google Scholar 

  75. Andrews P, Vetter W (1995) A systematic nomenclature system for toxaphene congeners. 1. Chlorinated bornanes. Chemosphere 31: 3879–3886

    Google Scholar 

  76. Oehme M, Kallenborn R (1995) A simple numerical code for polychlorinated compound classes allowing an unequivocal derivation of the steric structure. I. Polychlorinated biphenyls and bornanes. Chemosphere 30:1739–50; reply to comments (1995) 31: 3384–3385

    CAS  Google Scholar 

  77. Nikiforov VA, Tribulovich VG, Karavan, VS (1995) On the nomenclature of toxaphene congeners. Organohalogen Compd 26: 393–396

    CAS  Google Scholar 

  78. Jensen S (1966) Report of a new chemical hazard. New Sci 32: 612

    Google Scholar 

  79. Waid JS (1986) PCB and the environment. Vol I, CRC Press, Florida, pp 79–100

    Google Scholar 

  80. de Boer J (1988) Trends in chlorobiphenyl contents in livers of Atlantic cod (Gadus morhua) from the North Sea, 1979–1987. Chemosphere 17: 1811–1819

    Article  Google Scholar 

  81. Duinker JC, Hillebrand MTJ, Zeinstra T, Boon JP (1989) Individual chlorinated biphenyls and pesticides in tissues of some cetean species from the North Sea and the Atlantic Ocean. Tissue distribution and biotransformation. Aquatic Mammals 15: 95–124

    Google Scholar 

  82. Kallenborn R, Hühnerfuss H (1993) Vergleich der Verteilung von ausgewählten chlorierten organischen Schadstoffen in Eiderenten (Somateria mollissima L.) aus den Einzugsbereichen der Naturschutzgebiete Neuwerk and Oehe-Schleimünde. Seevögel 14: 23–31

    Google Scholar 

  83. Hühnerfuss H, Pfaffenberger B, Gehrcke B, Karbe L, König WA, Landgraff 0 (1995) Stereochemical effects of PCBs in the marine environment: seasonal variation of coplanar and atropisomeric PCBs in blue mussels (Mytilus edulis L.) of the German Bight. Mar Pollut Bull 30: 332–340

    Google Scholar 

  84. Kaiser KLE (1974) On the optical activity of polychlorinated biphenyls. Environ Pollut 7: 93–101

    Article  CAS  Google Scholar 

  85. Hühnerfuss H, Pfaffenberger B, Gehrcke B, Karbe L, König WA, Landgraff 0 (1994) Gas chromatographic enantiomer separation and potential toxicity of atropisomeric polychlorinated biphenyls in marine biota: has the toxic equivalence factor“TEF” concept to be expanded? Organohalogen Compd 21: 15–20

    Google Scholar 

  86. Haglund P (1995) Isolation of PCB atropisomers for toxicological testing using chiral high-performance liquid chromatography. Organohalogen Compd 23: 35–40

    CAS  Google Scholar 

  87. Schurig V, Glausch A, Fluck M (1995) On the enantiomerization barrier of atropisomeric 2,2’,3,3’,4,6’-hexachlorobiphenyl (PCB 132). Tetrahedron Asymmetry 6: 2161–2164

    Article  CAS  Google Scholar 

  88. Haglund P (1996) Enantioselective separation of polychlorinated biphenyl atropisomers using chiral high-performance liquid chromatography. J Chromatogr A 724: 219–228

    Article  CAS  Google Scholar 

  89. Haglund P (1996) Isolation and characterization of polychlorinated biphenyl (PCB) atropisomers. Chemosphere 32: 2133–2140

    Article  CAS  Google Scholar 

  90. Blanch GP, Glausch A, Schurig V, Serrano R, Gonzalez MJ (1996) Quantification and determination of enantiomeric ratios of chiral PCB 95, PCB 132, and PCB 149 in shark liver samples (C. coelolepis) from the Atlantic Ocean. J High Resolut Chromatogr 19: 392–396

    Article  CAS  Google Scholar 

  91. Ramos L, Jiménez B, Fernandez M, Hernandez L, Gonzalez MJ (1996) Coplanar and chiral PCB determinations using pyrenyl-silica HPLC and HRGC/ECD. Applications to real samples. Organohalogen Compd 27: 376–379

    Google Scholar 

  92. Müller U, Vetter W, Hummert K, Luckas B (1996) Levels and enantiomeric ratios of oxychlordane and a-HCH in harbour seals (Phoca vitulina) and grey seal (Halichoerus grypus) from Iceland. Organohalogen Compd 29: 118–121

    Google Scholar 

  93. Fowler J, Chen L (1990) Practical statistics for field biology. Open University Press, Milton Keynes, UK, pp 130–136

    Google Scholar 

  94. Rimkus G, Wolf M (1987) Schadstoffbelastung von Wild aus Schleswig-Holstein. 2. Mitteilung: Rückstände von Dieldrin, Heptachlorepoxid und anderen Cyclodien-Insektiziden im Leberfett von Hasen (Lepus europaeus L.) Z Lebensm Unters Forsch 184: 308–312

    Article  CAS  Google Scholar 

  95. Möller K (1993) Untersuchungen zur enantioselektiven Anreicherung von chiralen Schadstoffen im marinen und terrestrischen Ökosystem. Master thesis (Diplomarbeit), University of Hamburg, Hamburg, Germany, p 49

    Google Scholar 

  96. Pfaffenberger B (1995) Untersuchungen zur enantioselektiven Anreicherung von chiralen organischen Schadstoffen im marinen und terrestrischen Ökosystem. Dissertation, University of Hamburg, Verlag Shaker, Aachen, Germany, 182 pp

    Google Scholar 

  97. Hummert K, Vetter W, Luckas B (1995) Levels of a-HCH, lindane, and enantiomeric ratios of a-HCH in marine mammals from the northern hemisphere. Chemosphere 31: 3489–3500

    Article  CAS  Google Scholar 

  98. Klobes U, Vetter W, Luckas B, Hottinger G (1998) Enantioselective determination of 2endo,3-exo,5-endo,6-exo,8,8,9,10-octachlorobornane (B8–1412) in environmental samples. Organohalogen Compd 35: 359–362

    CAS  Google Scholar 

  99. Vetter W, Luckas B (1998) Analytical artifacts during enantioselective determination of chiral organochlorines with GC/ECNI-MS. Organohalogen Compd 35: 367–370

    CAS  Google Scholar 

  100. Reich S, Jiménez B, Marsili L, Hernandez LM, Schurig V, Gonzalez MJ (1998) Enantiomeric ratios of chiral PCBs in striped dolphins (Stenella coeruleoalba) from the Mediterranean Sea. Organohalogen Compd 35: 335–338

    Google Scholar 

  101. Jensen S, Jansson B (1976) Methyl sulphone metabolites of PCB and DDE. Ambio 5: 257–260

    CAS  Google Scholar 

  102. Kato Y, Haraguchi K, Kawashima M,Yamada S, Isogai M, Masuda Y, Kimura R (1995) Characterization of hepatic microsomal cytochrome P-450 from rats treated with methyl sulfonyl metabolites of polychlorinated biphenyl congeners. Chem Biol Interact 95: 269–278

    CAS  Google Scholar 

  103. Kato Y, Haraguchi K, Tomiyasu K, Saito H, Isogai M, Masuda Y, Kimura R (1997) Structure-dependent induction of CYP2B1/2 by 3-methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats. Environ Toxicol Pharmacol 3: 137–144

    Article  CAS  Google Scholar 

  104. Larsson C, Ellerichmann T, Franke S, Athanasiadou M, Hühnerfuss H, Bergman A (1999) Enantiomeric separation of chiral methylsulphonyl PCB congeners in liver and adipose tissue from rats dosed with A50. Organohalogen Compd 40: 427–430

    CAS  Google Scholar 

  105. Hühnerfuss H, Kallenborn R, König WA, Rimkus G (1992) Preferential enrichment of the (+)-a-hexachlorocyclohexane in cerebral matter of harbour seals. Organohalogen Compd 10: 97–100

    Google Scholar 

  106. Hühnerfuss H, Kallenborn R, Möller K, Pfaffenberger B, Rimkus G (1993) Enzymatic enantioselective degradation of a-hexachlorocyclohexane in different tissues of marine and terrestrial biota as determined by chiral gas chromatography. Proc 15th Int Symp on Gas Chromatogr, Riva, pp 576–581

    Google Scholar 

  107. Möller K (1993) Untersuchungen zur enantioselektiven Anreicherung von chiralen Schadstoffen im marinen und terrestrischen Ökosystem. Master thesis (Diplomarbeit), University of Hamburg, Hamburg, Germany, p 49

    Google Scholar 

  108. Portig J, Stein K, Vohland HW (1989) Preferential distribution of a-hexachlorocyclohexane into cerebral white matter. Xenobiotica 19: 123–130

    Article  CAS  Google Scholar 

  109. Gatermann R, Biselli S, Hühnerfuss H, Rimkus GG, Hecker M, Karbe L (2001) Synthetic musks in the environment. 1. Species-dependent bioaccumulation for HHCB, AHTN, musk xylene and musk ketone in freshwater fish. Submitted

    Google Scholar 

  110. Itrich NR, Simonich SL, Federle TW (1998) Biotransformation of the polycyclic musk, HHCB, during sewage treatment. Poster Presentation at the SETAC 19th Annual Meeting, 14–15 November, Charlotte, NC, USA

    Google Scholar 

  111. Hühnerfuss H, Gatermann R, Biselli S, Rimkus GG, Hecker M, Kallenborn R, Karbe L (1999) Enantioselective transformation of polycyclic musks in aquatic biota. Organo-halogen Compd 40: 401–404

    Google Scholar 

  112. Gatermann R, Hühnerfuss H, Biselli S, Rimkus GG, Hecker M, Kallenborn R, Karbe L (1999) Species-dependent enantioselective transformation of HHCB, AHTN and ATII in crucian carp (Carassius carassius) and tench (Tinca tinca). Organohalogen Compd 40: 595–598

    CAS  Google Scholar 

  113. Biselli S, Dittmer H, Gatermann R, Kallenborn R, König WA, Hühnerfuss H (1999) Separation of HHCB, ATII, AHDI and DPMI by enantioselective capillary gas chromatography and preparative separation of HHCB and ATII by enantioselective HPLC. Organohalogen Compd 40: 599–602

    Google Scholar 

  114. Ohloff G (1990) Riechstoffe und Geruchssinn–Die molekulare Welt der Düfte, Springer-Verlag, Berlin, Heidelberg, New York, pp 195–209

    Google Scholar 

  115. Rimkus GG (1999) Polycyclic musk fragrances in the aquatic environment. Toxicol Lett 111: 37–56

    Article  CAS  Google Scholar 

  116. Yamagishi T, Miyazaki T, Horii S, Kaneko S (1981) Identification of musk xylene and musk ketone in freshwater fish collected from the River Tama. Tokyo Bull Environ Contam Toxic 26: 656–662

    Article  CAS  Google Scholar 

  117. Yamagishi T, Miyazaki T, Horii S, Akiyama K (1983) Synthetic musk residues in biota and water from the River Tama and Tokyo Bay. Arch Environ Contam Toxicol 12: 83–89

    Article  CAS  Google Scholar 

  118. Gatermann R, Hühnerfuss H, Rimkus G, Wolf MS, Franke S (1995) The distribution of nitrobenzene and other nitroaromatic compounds in the North Sea. Mar Pollut Bull 30: 221–227

    Article  CAS  Google Scholar 

  119. Eschke HD, Traud J, Dibowski H-J (1994) Analytik und Befunde künstlicher Nitromoschussubstanzen in Oberflächen-und Abwässern sowie Fischen aus dem Einzugsgebiet der Ruhr. Vom Wasser 83: 373–383

    CAS  Google Scholar 

  120. Rimkus GG, Wolf M (1995) Nitro musk fragrances in biota from fresh-water and marine environment. Chemosphere 30: 641–651

    Article  CAS  Google Scholar 

  121. Rimkus GG, Rimkus B, Wolf M (1994) Nitro musks in human adipose tissue and breast milk. Chemosphere 28: 421–432

    Article  CAS  Google Scholar 

  122. Liebl B, Ehrenstorfer S (1993) Nitro musks in human milk. Chemosphere 27: 2253–2260

    Article  CAS  Google Scholar 

  123. Müller S, Schmid P, Schlatter C (1996) Occurrence of nitro and non-nitro benzenoid musk compounds in human adipose tissue. Chemosphere 33: 17–28

    Article  Google Scholar 

  124. Verordnung (EG) Nr. 143/97 der Kommission vom 27. Januar 1997 zur Festlegung der dritten Prioritätsliste gemäß der Verordnung (EWG) Nr. 793/93, Amtsblatt der Europäischen Gemeinschaften Nr.125/13

    Google Scholar 

  125. OSPAR convention for the protection of the marine environment of the North-East Atlantic ad hoc working group on the development of a dynamic selection and prioritisation mechanism for hazardous substances, Berlin 14–16. 9. 1998

    Google Scholar 

  126. Rimkus GG, Butte W, Geyer HJ (1997) Critical considerations on the analysis and bio-accumulation of musk xylene and other synthetic nitro musks in fish. Chemosphere 35: 1497–1507

    Article  CAS  Google Scholar 

  127. Gatermann R, Hühnerfuss H, Rimkus G, Attar A, Kettrup A (1998) Occurrence of musk xylene and musk ketone metabolites in the aquatic environment. Chemosphere 36: 2535–2547

    Article  CAS  Google Scholar 

  128. Rimkus GG (1998) Synthetic musk fragrances in human fat and their potential uptake by dermal resorption. In: Frosch PJ, Johansen JD, White IR (eds) Fragrances. Beneficial and adverse effects. Springer-Verlag, Berlin, Heidelberg, New York, p 136

    Google Scholar 

  129. van de Plassche EJ, Balk F (1997) Environmental risk assessment of the polycyclic musks AHTN and HHCB according to the EU-TGD. RIVM-Report No. 6011503008, Bilthoven

    Google Scholar 

  130. Eschke H-D, Traud J, Dibowski H-J (1994) Untersuchungen zum Vorkommen polycyclischer Moschus-Duftstoffe in verschiedenen Umweltkompartimenten - Nachweis und Analytik mit GC/MS in Oberflächen-, Abwässern und Fischen. UWSF-Z Umweltchem Okotox 6: 183–189

    Google Scholar 

  131. Eschke H-D, Dibowski H-J, Traud J (1995) Untersuchungen zum Vorkommen polycyclischer Moschus-Duftstoffe in verschiedenen Umweltkompartimenten. UWSF-Z Umweltchem Okotox 7: 131–135

    Article  CAS  Google Scholar 

  132. Rimkus G, Brunn H (1996) Synthetische Moschusduftstoffe - Anwendung, Anreicherung in der Umwelt und Toxikologie. 1. Herstellung, Anwendung, Vorkommen in Lebensmitteln, Aufnahme durch den Menschen. Ernährung-Umschau 43: 442–449

    Google Scholar 

  133. Brunn H, Rimkus G (1997) Synthetische Moschusduftstoffe - Anwendung, Anreicherung in der Umwelt und Toxikologie. 2. Toxikologie der synthetischen Moschusduftstoffe und Schlußfolgerungen. Ernährung-Umschau 44: 4–9

    Google Scholar 

  134. Franke S, Meyer C, Heinzel N, Gatermann R, Hühnerfuss H, Rimkus G, König WA, Francke W (1999) Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species. Chirality 11: 795–801

    Article  CAS  Google Scholar 

  135. Frater G, Müller U, Bajgrowicz JA, Petrzilka M (1995) Musky and odorless diastereo-mers of galaxolide. In: Baser KHC (ed) Flavours, fragrances and essential oils, Proc 13th Int Congress of flavours, fragrances and essential oils, Istanbul, Turkey, October 15–19

    Google Scholar 

  136. Müller S, Schmid P, Schlatter C (1996) Occurrence of nitro and non-nitro benzenoid musk compounds in human adipose tissue. Chemosphere 33: 17–28

    Article  Google Scholar 

  137. König WA (2000) Chirality in the natural world - odours and tastes. In: Wainer IW, Laugh J (eds) 150 Years after Pasteur. Kloever-Verlag, in press

    Google Scholar 

  138. Baydar A, Petrzilka M, Schott MP (1993) Olfactory threshold for androstene and Galaxolide: sensitivity, insensitivity and specific anosmia. Chem Senses 18: 661–668

    Article  CAS  Google Scholar 

  139. Gower DB, Ruparelia BA (1993) Olfaction in humans with special reference to odorous 16-androstenes: their occurrence, perception and possible social, psychological and sexual impact. J Endocrinol 137: 167–187

    Article  CAS  Google Scholar 

  140. Gilbert AN, Wysocki CJ (1991) Quantitative assessment of olfactory experience during pregnancy. Psychosomatic Medicine 53: 693–700

    CAS  Google Scholar 

  141. Buck L, Axel R (1991) A novel multigene family may encode odorant receptors: a molecular basis for odor recognition. Cell 65: 175–187

    Article  CAS  Google Scholar 

  142. Stacey NE, Sorensen PW, Cardwell JR (1993) Hormonal pheromones: recent developments and potential applications in aquaculture. Coastal and Estuarine Studies, Berlin, pp 227–239

    Google Scholar 

  143. Bjerselius R, Olsén KH (1993) The olfactory sensitivity of crucian carp (Carassius carassius) and goldfish (Carassius auratus) to 17,20b-dihydroxy-4-pregnen-3-one and prostaglandin F2. Chem Senses 18: 427–436

    Article  CAS  Google Scholar 

  144. Müller MD, Buser H-R (1995) Environmental behaviour of acetamide pesticide stereoisomers. 2. Stereo-and enantioselective degradation in sewage sludge and soil. Environ Sci Technol 29: 2031–2037

    Google Scholar 

  145. Vetter W, Bartha R, Stern G, Tomy G (1998) Enantioselective determination of two major compounds of technical toxaphene in Canadian lake sediment cores from the last 60 years. Organohalogen Compd 35: 343–346

    CAS  Google Scholar 

  146. Vetter W, Bartha R, Stern G, Tomy G (1999) Enantioselective determination of two persistent chlorobornane congeners in sediment from a toxaphene treated Yukon lake. Environ Toxicol Chem 18: 2775–2781

    Article  CAS  Google Scholar 

  147. Fingerling G, Hertkorn N, Parlar H (1996) Formation and spectroscopic investigation of two hexachlorobornanes from six environmentally relevant toxaphene components by reductive dechlorination in soil under anaerobic conditions. Environ Sci Technol 30: 2984–2992

    Article  CAS  Google Scholar 

  148. Rappe C, Haglund P, Buser H-R, Müller MD (1997) Enantioselective determination of chiral chlorobornanes in sediments from the Baltic Sea. Organohalogen Compd 31: 233–237

    CAS  Google Scholar 

  149. Benickâ E, Novakovski R, Hrouzek J, Krupcik J (1996) Multidimensional gas chromatographic separation of selected PCB atropisomers in technical formulations and sediments. J High Resolut Chromatogr 19: 95–98

    Article  Google Scholar 

  150. Ariëns EJ, van Rensen JJS, Welling W (1988) Stereoselectivity of pesticides. Biological and chemical problems. Elsevier, Amsterdam

    Google Scholar 

  151. Ramos Tombo GM, Bellus D (1991) Chiralität und Pflanzenschutz. Angew Chem 103: 1219–1241

    Article  CAS  Google Scholar 

  152. Buser H-P, Francotte E (1996) Stereoselective analysis in crop protection. In: Ahuja S (ed) Chiral separations: applications and technology. ACS Professional Reference Books, Washington, chap 5, pp 93–138

    Google Scholar 

  153. Bidleman TF, Jantunen LM, Harner T, Wiberg K, Wideman J, Falconer RL, Aigner EJ, Lenone AD, Ridal JJ, Kerman B, Parkhurst W, Finizio A, Szeto SY (1997) Chiral pesticides as tracers of air-surface exchange. Organohalogen Compd 31: 238–243

    CAS  Google Scholar 

  154. Wiberg K, Jantunen LM, Harner T, Wideman JL, Bidleman TF, Brice K, Su K, Falconer RL, Leone AD, Parkhurst W, Alegria H (1997) Chlordane enantiomers as source markers in ambient air. Organohalogen Compd 33: 209–213

    CAS  Google Scholar 

  155. Bidleman TF, Jantunen LM, Wiberg K, Harner T, Brice KA, Su K, Falconer RL, Leone AD, Aigner EJ, Parkhurst WJ (1998) Soil as a source of atmospheric heptachlor epoxide. Environ Sci Technol 32: 1546–1548

    Article  CAS  Google Scholar 

  156. Falconer R, Leone A, Bodnar C, Wiberg K, Bidleman T, Jantunen L, Harner T, Parkhurst W, Alegria H, Brice K, Su K (1998) Using enantiomeric ratios to determine sources of chlordane to ambient air. Organohalogen Compd 35: 331–334

    CAS  Google Scholar 

  157. Aigner E, Leone A, Falconer R (1998) Concentrations and enantiomers of pesticides in soil from the U.S. cornbelt. Environ Sci Technol 32: 1162–1168

    Article  CAS  Google Scholar 

  158. Bidleman T, Alegria H, Ngabe B, Green C (1998) Trends of chlordane and toxaphene in ambient air of Columbia, South Carolina. Atmos Environ 32: 1849–1856

    Google Scholar 

  159. Finizio A, Bidleman TF, Szeto SY (1998) Emission of chiral pesticides from an agricultural soil in the Fraser Valley, British Columbia. Chemosphere 36: 345–355

    Google Scholar 

  160. Falconer RL, Bidleman TF, Szeto SY (1997) Chiral pesticides in soils of the Fraser Valley, British Columbia. J Agric Food Chem 45: 1946–1951

    Google Scholar 

  161. Hühnerfuss H, Garrett WD (1981) Experimental sea slicks: their practical applications and utilization for basic studies of air-sea interactions. J Geophys Res 86: 439–447.

    Article  Google Scholar 

  162. Ulrich EM, Hites RA (1998) Enantiomeric ratios of chlordane-related compounds in air near the Great Lakes. Environ Sci Technol 32: 1870–1874

    Article  CAS  Google Scholar 

  163. Kallenborn R, Hartwig E, Hühnerfuss H (1994) Vergleich der Nahrung der Eiderenten (Somateria mollissima L.) aus unterschiedlichen Rastgebieten. Seevögel 15: 31–37.

    Google Scholar 

  164. Lewis DL, Garrison AW, Wommack KE, Whittemore A, Steudler P, Melillo J (1999) Influence of environmental changes on degradation of chiral pollutants in soils. Nature: 401: 898–901

    Article  CAS  Google Scholar 

  165. de Geus HJ, Baycan-Keller R, Oehme M, de Boer J, Brinkman UATh (1998) Enantiomer ratios of bornane congeners in biological samples using heart-cut gas chromatography with an enantioselective column. J High Resolut Chromatogr 21: 39–46

    Article  Google Scholar 

  166. Karlsson H, Oehme M, Scherer G (1998) Structure elucidation of U82, a major octachloro chlordane congener present at higher trophic levels in marine food webs and in human tissue. Organohalogen Compd 35: 51–55

    CAS  Google Scholar 

  167. Karlsson H, Oehme M, Scherer G (1999) Isolation of the chlordane compounds U82, MC5, MC7, and MC8 from technical chlordane by HPLC including structure elucidation of U82 and determination of ECD and NICI-MS response factors. Environ Sci Technol 33: 1353–1358

    Article  CAS  Google Scholar 

  168. Weigel S (1998) Entwicklung einer Methode zur Extraktion organischer Spurenstoffe aus großvolumigen Wasserproben mittels Festphasen. Master thesis ( Diplomarbeit ), University of Hamburg, p 86

    Google Scholar 

  169. Buser H-R, Poiger T, Müller MD (1999) Occurrence and environmental behaviour of the chiral pharmaceutical drug ibuprofen in surface waters and in wastewater. Environ Sci Technol 33: 2529–2535

    Article  CAS  Google Scholar 

  170. Ternes T (1998) Occurrence of drugs in German sewage treatment plants and rivers. Water Res 32: 3245–3260

    Article  CAS  Google Scholar 

  171. Harju MT, Haglund P (1999) Determination of rotational barriers of atropisomeric polychlorinated biphenyls. J Anal Chem 364: 219–223

    Article  CAS  Google Scholar 

  172. Ellerichmann T (2000) Analyse chiraler PCB and ihrer Methylsulfonyl-Metaboliten in Biotaproben mit Hilfe enantioselektiver Gas-and Flüssigkeitschromatographie unter Verwendung von Cyclodextrinderivaten. PhD thesis, University of Hamburg, Verlag Shaker, Aachen, Germany, p 118

    Google Scholar 

  173. Biselli S (2001) PhD thesis, University of Hamburg, in preparation

    Google Scholar 

  174. Pfeiffer CC (1956) Optical isomerism and pharmacological action, a generalization. Science 124: 29–41

    Article  CAS  Google Scholar 

  175. Buser H-R, Müller MD (1995) Isomer-selective and enantiomer-selective determination of DDT and related compounds using chiral high-resolution gas chromatography/mass spectrometry and chiral HPLC. Anal Chem 67: 2691–2698

    Article  CAS  Google Scholar 

  176. Rimkus GG, Wolf M (1993) Contaminants in fish from aquaculture. 2. Musk xylene and musk ketone contaminants in fish. Dts Lebensmittel-Rundschau 89: 171–175

    Google Scholar 

  177. Vetter W (1993) Toxaphene–Theoretical aspects of the distribution of chlorinated bornanes including symmetry aspects. Chemosphere 26: 1079–1084

    Article  CAS  Google Scholar 

  178. BidlemanTF, Falconer RL (1999) Enantiomer ratios for apportioning two sources of chiral compounds. Environ Sci Technol 33: 2299–2301

    Article  Google Scholar 

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Kallenborn, R., Hühnerfuss, H. (2001). Chiral Xenobiotics in the Environment. In: Chiral Environmental Pollutants. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-06243-2_3

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