Chromatographic enrichment and enantiomer separation of axially chiral polybrominated biphenyls in a technical mixture

Berger, Urs; Vetter, Walter; Götsch, Arntraut; Kallenborn, Roland

doi:10.1016/s0021-9673(02)01112-3

Cited by 24 publications

(16 citation statements)

References 30 publications

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“…However, due to their more bulky bromine substituents, it can be assumed that more than 19 atropisomeric forms (like the ones for PCBs) exist at ambient temperature. Up to now, few atropisomers have been identified [79,80] and separated by GC or HPLC. To our knowledge, no method has been developed till now for the chiral separation of PBBs atropisomers by CE, constituting other research line to be explored.…”

Section: Chiral Analysis Of Other Pollutantsmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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Chiral analysis of pollutants and their metabolites by capillary electromigration methodsChiral separation of enantiomers is one of the most challenging tasks for any analytical technique including CE. Since the first report in 1985 showing the great possibilities of CE for the separation of chiral compounds, the amount of publications concerning this topic has quickly increased. Although chiral electromigration methods have mainly been used for enantioseparation of drugs and pharmaceuticals, they have also been applied to analyze chiral pollutants. This article intends to provide an updated overview, including works published till January 2005, on the principal applications of CE to the chiral analysis of pollutants and their metabolites, with especial emphasis on articles published in the last 10 years. The main advantages and drawbacks regarding the use of CE for chiral separation of pollutants are addressed including some discussion on the foreseen trends of electromigration procedures applied to chiral analysis of contaminants. IntroductionSeparation of chiral compounds is an interesting and challenging topic of research in many analytical chemistry areas, especially in the biomedical, pharmaceutical, and environmental fields where pure enantiomeric forms are widely required. It is already well-known that enantiomers, in spite of their very similar structure, when exposed to an identical biological environment can show very different biological activity. Furthermore, as a general rule, when the toxicological effect of an active substance is directly related to its desired biological activity, the most active isomer is usually the most toxic one Abbreviations: Allyl-TER, 1-allylterguride; ANDSA, 7-aminonaphthalene-1,3-disulfonic acid; ANSA, 5-aminonaphthalene-1-sulfonic acid; ANTS, 8-aminonaphthalene-1,3,6-trisulfonic acid; CA, chrysanthemic acid; CM-ª-CD, carboxymethylated-g-CD; CMBA, 2-(4-chlorophenyl)-3-methylbutanoic acid; 2,2-CPPA, 2-(2-chlorophenoxy)-propionic acid; 2,3-CPPA, 2-(3-chlorophenoxy)-propionic acid; 2,4-CPPA, 2-(4-chlorophenoxy)-propionic acid; â-CD-NH 2 , 6-monodeoxy-6-monoamino-b-CD; â-CD- (NH 3 )

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Section: Chiral Analysis Of Other Pollutantsmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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“…Using enantioselective high‐performance liquid chromatography (HPLC), and lowering the temperature to ∼0 °C, did not resolve PCB 153, but did resolve two other environmentally relevant di‐ ortho congeners, i.e., PCB 170 and PCB 194 . In the case of more bulky bromine substituents, instead of chlorine, several PBB congeners were partly resolved by enantioselective HPLC at ∼25 °C …”

Section: The Two Faces Of Polychlorinated Compoundsmentioning

confidence: 99%

Gas Chromatographic Enantiomer Separation of Polychlorinated Biphenyls (PCBs): Methods, Metabolisms, Enantiomeric Composition in Environmental Samples and their Interpretation

Vetter

2016

Israel Journal of Chemistry

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The year 2016 not only marks the 50th anniversary of the first successful discovery of gas chromatographic (GC) enantiomer separations in 1966 by Gil‐Av, but also the less appraised 50th anniversary of the discovery of polychlorinated biphenyls (PCBs) in the environment. This article reports on GC enantiomer separations of axially stable, chiral PCBs (PCB atropisomers) with modified cyclodextrins. Nineteen atropisomeric PCBs exist, but most data exists for four PCB atropisomers (PCB 95, PCB 132, PCB 149, and PCB 136), which can be resolved without significant coelutions on three columns coated with modified cyclodextrins. Nonracemic compositions of PCB atropisomers and their hydroxylated metabolites have been documented in various studies. However, the measured enantiomer fractions are currently difficult to interpret und understand. The most plausible reasons for these difficulties are discussed and interpreted with the help of selected examples from the literature.

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“…Polybrominated biphenyls, like PCBs, were used as capacitor fluids in mixtures of congeners (e.g. Firemaster), and are also atropisomeric [4]. While HBCDD is the most common chiral brominated flame retardant, others exist, such as 2,3-dibromopropyl-2,4,6-tribromophenyl ether (Figure 4.7).…”

Section: Brominated Flame Retardants (See Also Chapter 2)mentioning

confidence: 99%

“…A number of the organochlorine (OC) pesticides are also chiral: the technical dichlorodiphenyltrichloroethane (DDT) component o,p 0 -DDT and its anaerobic metabolite o,p 0 -DDD; a-hexachlorocyclohexane (a-HCH), the only chiral isomer of technical HCH; many of the cyclodienes in the chlordane class, including major components cis-and trans-chlordane and heptachlor, minor components such as MC-5, MC-6, MC-7, and U82, and degradates such as oxychlordane and heptachlor epoxide; and most of the possible chlorobornane congeners of toxaphene [3]. Many emerging POPs are also chiral, such as pyrethroid insecticides, hexabromocyclododecane (HBCDD), other brominated flame retardants such as polybrominated biphenyls (PBBs) [4] and some ethers [5], and PCB metabolites such as hydroxylated [6] and methylsulfonyl PCBs [7]. Surprisingly, the chirality of pollutants has received relatively limited attention, despite the significantly different toxicity that enantiomers may have compared to each other and to the racemate, and the insights that enantiomer analysis can bring to understanding processes affecting pollutants in the environment.…”

Section: Introductionmentioning

confidence: 99%

Chirality as an Environmental Forensics Tool

Wong

Warner

2009

Persistent Organic Pollutants

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Chromatographic enrichment and enantiomer separation of axially chiral polybrominated biphenyls in a technical mixture

Cited by 24 publications

References 30 publications

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Gas Chromatographic Enantiomer Separation of Polychlorinated Biphenyls (PCBs): Methods, Metabolisms, Enantiomeric Composition in Environmental Samples and their Interpretation

Chirality as an Environmental Forensics Tool

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