Enantiomer separation of atropisomeric polychlorinated biphenyls (PCBs) by gas chromatography on Chirasil-Dex

Schurig, Volker; Glausch, Alexandra

doi:10.1007/bf01136039

Cited by 56 publications

(24 citation statements)

References 11 publications

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“…39 In further studies, the merit and limit of enantioselective chromatography for determining small deviations from racemic compositions of other classes of chiral compounds should be explored. This applies for example to chiral persistent organic pollutants (POPs) that are released as synthetic racemates in the environment but are prone to enantioselective degradation in biota 40 allowing the specific fate of chiral pesticides in the environment to be traced. Some initial data have already been published in the literature.…”

Section: à13mentioning

confidence: 99%

Evaluation of enantioselective gas chromatography for the determination of minute deviations from racemic composition of α‐amino acids with emphasis on tyrosine: Accuracy and precision of the method

et al. 2007

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Whereas the determination of high enantiomeric fractions (EF) of chiral compounds is very well established, the accurate determination of small deviations from racemic compositions has not yet received much attention despite its relevance to studies dealing with the origin of homochirality, where only small initial enantiomeric bias is expected. Racemic samples of representative alpha-amino acids were derivatized as N-(O,S)-trifluoroacetyl/ethylesters and analyzed by enantioselective gas chromatography (GC) on fused silica capillaries coated with the chiral stationary phases (CSPs) Chirasil-D-Val, Chirasil-L-Val, and Lipodex E with GC/FID and GC/MS detection. The validation (accuracy and precision) of the determination of the enantiomeric fraction EF of the D-enantiomer in racemic or near-racemic compositions for 10 DL-alpha-amino acids obtained from commercial sources has been carried out. Emphasis is given to DL-tyrosine, the enantiomers of which have recently been claimed to show different crystallization properties. Values of EF obtained from GC measurements using CSPs were compared with those from CE using chiral mobile phase additives. While the precision of the GC method is generally better than 0.08% for all DL-alpha-amino acids studied, accuracy (trueness) of determination of amino acids with polar side chains is poorer than expected from the precision as a result of systematic errors. The accuracy determined relied on measurements on two oppositely configurated CSPs.

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Section: à13mentioning

confidence: 99%

Evaluation of enantioselective gas chromatography for the determination of minute deviations from racemic composition of α‐amino acids with emphasis on tyrosine: Accuracy and precision of the method

et al. 2007

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“…However, only in few occasions chiral PCBs were separated. Separation of chiral PCBs are currently performed by capillary gas chromatography (GC) [3,[11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of polychlorinated biphenyls using a combination of hydroxypropyl-γ-cyclodextrin and a polymeric chiral surfactant

Edwards

Shamsi

2002

Electrophoresis

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Chiral separation of moderately to highly hydrophobic polychlorinated biphenyls (PCBs) using a conventional chiral micelle or a polymeric chiral surfactant, as the single chiral selector is very difficult since the hydrophobic interactions between the chiral PCB and the monomeric or polymeric surfactant is very strong. Combined use of a polymeric chiral surfactant, polysodium N-undecanoyl-D-valinate (poly-D-SUV) with hydroxypropyl-gamma-cyclodextrin (HP-gamma-CD) was successful in cyclodextrin modified electrokinetic chromatography (CD-EKC) enantioseparation of PCB congeners. Addition of HP-gamma-CD to the background electrolyte containing poly-D-SUV functioned to improved chiral resolution for the PCBs and reduce the analysis time for these congeners. In addition, concentration of methanol, concentration of 2-(N-cyclohexylamino) ethanesulfonic acid (CHES) buffer and separation voltage was also varied to optimize multicomponent separation of five chiral PCBs. Simultaneous separation and enantioseparation of all five PCBs was possible in less than 50 min under optimized conditions that requires a 5 mM CHES solution buffered at about pH 10 with 1.5% w/v (ca. 60 mM) poly-D-SUV and 16 mM HP-gamma-CD. In addition, 1 M urea and 20% v/v methanol should be added as organic modifier and the capillary temperature maintained at 45 degrees C. As expected the polymeric surfactant showed improved chiral resolution of PCBs over conventional micelles of SUV. Under optimized conditions, when CD-EKC of chiral PCBs using poly-D-SUV was compared to sodium dodecyl sulfate (SDS), better resolution, higher efficiency and shorter analysis time was achieved with poly-D-SUV.

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“…The concept of atropisomerism in drug discovery has been properly discussed in several papers [4][5][6]. The detailed investigations on the rotational barriers in relation to the substituents and substitution pattern of biphenyl congeners were carried out by the research groups of Schurig et al [7] and König et al [8]. Like traditional racemic material, atropisomers with a large energy barrier can be isolated by traditional enantioselective chromatography, crystallization, or classic resolution.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic resolution of atropisomers for toxicity and biotransformation studies in pharmaceutical research

Yan

Riley

Philippe

et al. 2015

Journal of Chromatography A

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Enantiomer separation of atropisomeric polychlorinated biphenyls (PCBs) by gas chromatography on Chirasil-Dex

Cited by 56 publications

References 11 publications

Evaluation of enantioselective gas chromatography for the determination of minute deviations from racemic composition of α‐amino acids with emphasis on tyrosine: Accuracy and precision of the method

Evaluation of enantioselective gas chromatography for the determination of minute deviations from racemic composition of α‐amino acids with emphasis on tyrosine: Accuracy and precision of the method

Chiral separation of polychlorinated biphenyls using a combination of hydroxypropyl-γ-cyclodextrin and a polymeric chiral surfactant

Chromatographic resolution of atropisomers for toxicity and biotransformation studies in pharmaceutical research

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