Enantioselective semipreparative HPLC separation of PCB metabolites and their absolute structure elucidation using electronic and vibrational circular dichroism

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Autor/in:
Erscheinungsjahr:
2005
Medientyp:
Text
Schlagworte:
  • Ab initio DFT calculation
  • Electronic circular dichroism
  • Hydroxy PCB
  • Methoxy PCB
  • Methylsulfonyl PCB
  • Methylthionyl PCB
  • PCB metabolite enantiomers
  • Permethylated β-cyclodextrin
  • Semipreparative enantioselective HPLC
  • Vibrational circular dichroism
Beschreibung:
  • Polychlorinated biphenyls (PCBs) remain one of the most important groups of environmental contaminants. The fate (transformation) as well as the toxicological implications of the different metabolism steps are subject to considerable debate. The aim of this study is to start a comprehensive investigation of atropisomeric PCB metabolites, i.e., hydroxy, methoxy, methylthionyl, and methylsulfonyl PCBs in different biota. For this purpose, enantioselective semipreparative liquid chromatography is used to obtain pure enantiomers of PCB metabolites. Electronic circular dichroism (UV-CD) and vibrational circular dichroism (VCD) in combination with computational techniques were applied to determine their absolute structures. Approximately 18-25 mg of each enantiomer of the following metabolites were obtained using semipreparative HPLC on β-cyclodextrin-based columns: 4-MeO-CB149, 4-MeS-CB149, 4-MeSO2-CB149, 3-MeS-CB149, and 3-MeSO 2-CB149. The enantiomeric purity of the separated enantiomers was in the range of 95.0-99.9%. Rotational angles and absolute configurations were also determined. This study establishes a sound method for future preparation and absolute structure determination of compounds belonging to the same class. © 2005 Wiley-Liss, Inc.
Lizenz:
  • info:eu-repo/semantics/closedAccess
Quellsystem:
Forschungsinformationssystem der UHH
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oai:www.edit.fis.uni-hamburg.de:publications/a9a50fb1-6560-465d-8e70-2eeb2477077a