Gas chromatographic separation of the enantiomers of marine pollutants. 4. Fate of hexachlorocyclohexane isomers in the Baltic and North Sea

Huehnerfuss, Heinrich; Faller, Joern; Koenig, W. A.; Ludwig, Peter

doi:10.1021/es00035a009

Cited by 67 publications

(52 citation statements)

References 9 publications

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“…Until the last decade, enantioselective studies for analysis of chiral compounds in the environment employed CD-based CSPs [61,85,[96][97][98][99] or indirect methods using enantiomerically-pure derivatizing reagents [9,60], which have been used until today [67,70,80,83,89]. Since 2010, a trend is being verified for the use of three types of CSPs: protein-based [68,69,[74][75][76][77]81,82,100,101], polysaccharide-based [54,55,78,79,102] and macrocyclic antibiotic-based CSPs [13,26,27,63,64,71-73, 76,78,88,91,103].…”

Section: Basic Concepts Of Chiralitymentioning

confidence: 99%

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Ribeiro

Maia

et al. 2017

Symmetry

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Abstract: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.

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Section: Basic Concepts Of Chiralitymentioning

confidence: 99%

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Ribeiro

Maia

et al. 2017

Symmetry

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“…Su ortamında, kiral kirleticilerin analizinde α-HCH'ın enantiyoseçici parçalanması üzerine yapılmış çalışmalar [23], [75] öncü olmuştur. α-HCH, günümüzde, su ortamında en fazla çalışmaya konu olan kiral kirletici olmuştur [93].…”

Section: Kiral Bileşiklerin çEvredeki Akıbetiunclassified

Chiral pollutants and their significance in the environment

Can‐Güven¹,

Bolat²,

Gedik³

et al. 2016

Pamukkale J Eng Sci

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“…15) (ϩ)-Enantiomer of fipronil (4), a phenylpyrazole broad-spectrum insecticide, was more toxic to C. dubia than the (Ϫ)-enantiomer 16) but in other studies the (Ϫ)-enantiomer was shown to have significantly more androgen and progesterone activity than the (ϩ) form. 3) Enantioselective degradation occurred in human breast milk for o,pЈ-DDT (17), trans-chlordane (18), cis-chlordane (19), oxychlordane (20) and hexachlorocyclohexane (21) (Fig. 5), although pesticide levels were near or at detection limits for most compounds, 17) however, changes in enantiomeric composition are still not well understood, and further investigation in this direction is recommended.…”

Section: Biological Significance Of Chiral Isomersmentioning

confidence: 99%

“…Studies on chiral pesticides started to appear in the early 1990s. [19][20][21][22][23][24][25][26][27][28] Companies have been deeply interested in selling synthetic chiral pesticides as single enantiomers in the past decade. The key reasons why single isomers are less common than they could be are probably limited access to chiral raw materials and economic synthetic routes.…”

Section: Chirality and Potential For Pesticide Reductionmentioning

confidence: 99%

Chiral pesticides

Sekhon

2009

Journal of Pesticide Science

109

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The enantiomers of chiral pesticides are often metabolized at different rates. In agriculture, the preferred chiral form of a pesticide is more effective at lower application rates or more specific toward a targeted pest. Other advantages of chiral pure pesticides include greater environmental safety, reduced cost, greater specificity and extended patent life. Recent progress in optical resolution, asymmetric synthesis and biocatalysis of chiral pesticides has been described. Techniques to separate enantiomers with chiral HPLC and GC columns, electrophoresis and mass spectrometry have been reported. Chiral chase is actively pursuing asymmetric hydrogenation for the manufacture of a pure single-enantiomer pesticide. Enantioselectivity occurs in pesticidal activities toward target organisms as well as non-targeted organisms. There is a need to characterize both enantiomers of chiral pesticides in order to have an accurate understanding of their distribution and fate in the environment. Enantiomeric analysis can be useful in this aim and this is an important consideration in the risk assessment of pesticides. Use of only the target-active enantiomer of pesticides should be encouraged as it will reduce the pollutant load, provided it has no adverse impact on non-target organisms.

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Gas chromatographic separation of the enantiomers of marine pollutants. 4. Fate of hexachlorocyclohexane isomers in the Baltic and North Sea

Cited by 67 publications

References 9 publications

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Chiral pollutants and their significance in the environment

Chiral pesticides

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