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Environmental fate processes and biochemical transformations of chiral emerging organic pollutants

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Abstract

This review highlights the analytical chemistry, environmental occurrence, and environmental fate of individual stereoisomers of chiral emerging pollutants, which are modern current-use chemicals of growing environmental concern due to their presence in the environment and potential for deleterious effects. Comparatively little is known about individual stereoisomers of pollutants, which can have differential toxicological effects and can be tracers of biochemical weathering in the environment. Stereoisomers are resolved by gas chromatography (GC), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE). Separation techniques in environmental analysis are typically coupled to mass spectrometry (MS) and tandem mass spectrometry (MS/MS), as these provide the sensitivity and selectivity needed. The enantiomer composition of phenoxyalkanoic and acetamide herbicides, organophosphorus and pyrethroid pesticides, chiral polychlorinated biphenyl metabolites, synthetic musks, hexabromocyclododecane, and pharmaceuticals in the environment show species-dependent enantioselectivity from biotransformation and other biologically mediated processes affecting enantiomers differentially. These enantiomer compositions are useful in detecting biologically mediated environmental reactions, apportioning sources of pollutants, and gaining insight into the biochemical fate of chiral pollutants in the environment, which are needed for accurate risk assessment of such chemicals.

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Abbreviations

CE:

capillary electrophoresis

CZE:

capillary zone electrophoresis

AHDI:

synthetic musk 6-acetyl-1,1,2,3,3,5-hexamethyldihydroindene

AHTN:

synthetic musk 7-acetyl-1,1,3,4,4,6-hexamethyltetralin

ATII:

synthetic musk 5-acetyl-1,1,2,6-tetramethyl-3-isopropylindene

DDT:

dichlorodiphenyltrichloroethane

ECD:

electron capture detector

ECNI:

electron capture negative ionization

GC:

gas chromatography

GC/MS:

gas chromatography/mass spectrometry

HBCDD:

hexabromocyclododecane

HHCB:

synthetic musk 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-γ-2-benzopyran

HPLC:

high-performance liquid chromatography

HPLC/MS/MS:

high-performance liquid chromatography–tandem mass spectrometry

MEKC:

micellar electrokinetic chromatography

MeSO 2-PCB:

polychlorinated biphenyl methyl sulfone

MS:

mass spectrometry

MS/MS:

tandem mass spectrometry

NP:

normal phase

NSAID:

non-steroidal anti-inflammatory drugs

PCB:

polychlorinated biphenyl

POP:

persistent organic pollutant

RP:

reversed phase

OPs:

organophosphorus pesticides

UV:

ultraviolet detection

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  1. Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr., Edmonton, AB T6G 2G2, Canada

    Charles S. Wong

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Wong, C.S. Environmental fate processes and biochemical transformations of chiral emerging organic pollutants. Anal Bioanal Chem 386, 544–558 (2006). https://doi.org/10.1007/s00216-006-0424-3

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