Journal article
Absolute configuration of 2,2',3,3',6-pentachlorinatedbiphenyl (PCB 84) atropisomers
Environmental science and pollution research international, Vol.25(17), pp.16402-16410
06/2018
DOI: 10.1007/s11356-017-9259-z
PMCID: PMC5823790
PMID: 28537024
Abstract
Nineteen polychlorinated biphenyl (PCB) congeners, such as 2,2',3,3',6-pentachlorobiphenyl (PCB 84), display axial chirality because they form stable rotational isomers, or atropisomers, that are non-superimposable mirror images of each other. Although chiral PCBs undergo atropselective biotransformation and atropselectively alter biological processes, the absolute structure of only a few PCB atropisomers has been determined experimentally. To help close this knowledge gap, pure PCB 84 atropisomers were obtained by semi-preparative liquid chromatography with two serially connected Nucleodex β-PM columns. The absolute configuration of both atropisomers was determined by X-ray single-crystal diffraction. The PCB 84 atropisomer eluting first and second on the Nucleodex β-PM column correspond to (aR)-(-)-PCB 84 and (aS)-(+)-PCB 84, respectively. Enantioselective gas chromatographic analysis with the β-cyclodextrin-based CP-Chirasil-Dex CB gas chromatography column showed the same elution order as the Nucleodex β-PM column. Based on earlier reports, the atropisomers eluting first and second on the BGB-172 gas chromatography column are (aR)-(-)-PCB 84 and (aS)-(+)-PCB 84, respectively. An inversion of the elution order is observed on the Cyclosil-B gas chromatography and Cellulose-3 liquid chromatography columns. These results advance the interpretation of environmental and human biomonitoring as well as toxicological studies.
Details
- Title: Subtitle
- Absolute configuration of 2,2',3,3',6-pentachlorinatedbiphenyl (PCB 84) atropisomers
- Creators
- Xueshu Li - Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA, 52242, USASean R Parkin - Department of Chemistry, University of Kentucky, Lexington, KY, 40506, USAHans-Joachim Lehmler - Department of Occupational and Environmental Health, College of Public Health, The University of Iowa, Iowa City, IA, 52242, USA. hans-joachim-lehmler@uiowa.edu
- Resource Type
- Journal article
- Publication Details
- Environmental science and pollution research international, Vol.25(17), pp.16402-16410
- DOI
- 10.1007/s11356-017-9259-z
- PMID
- 28537024
- PMCID
- PMC5823790
- NLM abbreviation
- Environ Sci Pollut Res Int
- ISSN
- 0944-1344
- eISSN
- 1614-7499
- Publisher
- Germany
- Grant note
- P30 ES005605 / NIEHS NIH HHS R01 ES017425 / NIEHS NIH HHS ES017425 / National Institute of Environmental Health Sciences P42 ES013661 / NIEHS NIH HHS MRI CHE0319176 / National Science Foundation ES005605 / National Institute of Environmental Health Sciences ES013661 / National Institute of Environmental Health Sciences R13 ES027325 / NIEHS NIH HHS
- Language
- English
- Date published
- 06/2018
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute; Iowa Superfund Research Program
- Record Identifier
- 9984065387202771
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