Application of well-defined ?-cyclodextrins for the enantioseparation of compounds of technical toxaphene and further organochlorines

Ruppe, Steffen; Vetter, Walter; Luckas, Bernd; Hottinger, Georg

doi:10.1002/1520-667x(2000)12:10<541::aid-mcs3>3.0.co;2-q

Cited by 7 publications

(5 citation statements)

References 19 publications

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“…Note also that, depending on the substituents, the molecular weights of modified cyclodextrins are significantly higher than those of the native cyclodextrins (see Table 2). Purity-dependent variations in enantioseparations have also been reported for organochlorines (40,(67)(68)(69)(70)(71). However, as for most chemical syntheses, synthesis of CSPs cannot be performed quantitatively.…”

Section: Synthesis and Quality Of Modified Cyclodextrinsmentioning

confidence: 96%

“…Recent research is directed to gain well-defined fractions from crude products (68,71,72). It is widely accepted that non-reproducible CSPs are not desired but indispensable to some degree as some organochlorines have not been separated on well-defined CSPs (see below).…”

Section: Synthesis and Quality Of Modified Cyclodextrinsmentioning

confidence: 99%

“…CD-β-PMCD successfully separated many PCB atropisomers (see Table 3) and also several CTTs (105), which is in contrast to PD-β-PMCD (71). Although initial studies revealed comparable separation characteristics for α-HCH and PCCH enantiomers (23), significant differences exist between PDand CB-β-PMCD for other organochlorines.…”

Section: Permethyl-cyclodextrinmentioning

confidence: 99%

“…It was long thought that this is the only suitable CSP (75,135,40,(193)(194)(195)(196)(197)(198). Recently, it was found that only CB-β-PMCD and not PD-β-PMCD separated CTT enantiomers (71). Recently, it was found that only CB-β-PMCD and not PD-β-PMCD separated CTT enantiomers (71).…”

Section: Vettermentioning

confidence: 99%

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Enantioselective Fate of Chiral Chlorinated Hydrocarbons and Their Metabolites in Environmental Samples

Vetter

2001

Food Reviews International

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Gas chromatographic enantioseparation of chiral organochlorines (α-HCH, cis-and trans-chlordane, heptachlor, heptachlor epoxide, oxychlordane, o, p -DDT, compounds of technical toxaphene, stable atropisomeric PCBs and methylsulfonyl-PCBs) has been achieved during the last decade. For this purpose chiral stationary phases based on cyclodextrin derivatives have been applied in combination with GC/ECD, GC/MS, MDGC, and MS/MS. With these techniques methods have been developed which have been used to study the enantioselective fate of the chiral organochlorines. Changes in the enantioratios and conclusions drawn are reviewed. phenomenon of plane-polarized light (Malus, 1809) and optical rotation (Biot,113

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Section: Synthesis and Quality Of Modified Cyclodextrinsmentioning

confidence: 96%

Section: Synthesis and Quality Of Modified Cyclodextrinsmentioning

confidence: 99%

Section: Permethyl-cyclodextrinmentioning

confidence: 99%

Section: Vettermentioning

confidence: 99%

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Enantioselective Fate of Chiral Chlorinated Hydrocarbons and Their Metabolites in Environmental Samples

Vetter

2001

Food Reviews International

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“…Asztemborska et al reported on the dependence of retention and selectivity parameters of camphor enantiomers on the concentration of R-and β-CDs studied under conditions of gas-liquid chromatography and reversed-phase HPLC systems and relatively considerable differences were observed between stability constants detected by the different systems (84). Chiral organochlorines were enantioresolved on 11 GC columns containing different modified CDs whose structures were well-defined by HPLC-mass spectrometry (85). A novel procedure was proposed by Krupcik et al for the calculation of Gibbs energy corresponding to enantioselective interactions of 2-2,4-dinitrophenoxy-, 2-phenoxy-, and 2-halogenn-pentane enantiomers with a ChirasilDex CSP GC column, in which the energy is calculated from retention data as a difference between the Gibbs energy of an enantiomer and its corresponding achiral congener (86).…”

Section: Gas Chromatographymentioning

confidence: 99%

Chiral Separations

Ward

2002

Anal. Chem.

123

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Chiral Environmental Contaminants

Wong

Elmayergi

2009

Encyclopedia of Analytical Chemistry

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This article highlights techniques by which the enantiomers of chiral environmental pollutants can be separated and quantified. A large number of organic chemicals are chiral and exist as pairs of mirror images called enantiomers . These chemicals include legacy persistent organic pollutants (POPs) (e.g. polychlorinated biphenyls (PCBs)) and pesticides (e.g. dichlorodiphenyltrichloroethane (DDT)), as well as current‐use pesticides (e.g. pyrethroids), flame retardants (e.g. hexabromocyclododecane), and pharmaceuticals (e.g. ibuprofen). Understanding the environmental behavior of chiral xenobiotic compounds is important because enantiomers of a chiral compound may have different biological and toxicological effects, which must be delineated for accurate risk assessment of hazards, if any, posed by such chemicals. In addition, chiral chemicals are markers of biochemical activity in the environment, as enantiomer compositions are unaffected by physical and chemical processes but can change from differential enantiomer interactions with other chiral molecules (e.g. enzymes). For these reasons, the chirality of environmental pollutant occurrence, fate, and effects has been studied since the 1990s, when analytical capacity to measure chiral chemicals became widely available. We discuss major techniques for separating pollutant enantiomers including gas chromatography (GC), high‐performance liquid chromatography (HPLC), and capillary electrophoresis (CE). Enantioselective analytical separations are often coupled to mass spectrometry (MS) and tandem mass spectrometry (MS/MS) for quantification under environmentally relevant conditions (i.e. low concentrations to parts per trillion and below, in highly complex matrices such as wastewater and biological tissues). Issues involving sample preparation, data handling, and quality assurance/quality control are also described. Finally, we also illustrate applications of enantiomer‐specific measurements to gain insights into pollutants affecting environmental processes that could otherwise not be obtained, such as assessing pollutant biodegradation and delineating pollutant sources.

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Application of well-defined ?-cyclodextrins for the enantioseparation of compounds of technical toxaphene and further organochlorines

Cited by 7 publications

References 19 publications

Enantioselective Fate of Chiral Chlorinated Hydrocarbons and Their Metabolites in Environmental Samples

Enantioselective Fate of Chiral Chlorinated Hydrocarbons and Their Metabolites in Environmental Samples

Chiral Separations

Chiral Environmental Contaminants

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