Polychlorinated biphenyls chirality

Bordajandi, L.R., Korytar, P., De Boer, J., Gonzalez, M.J. (2005). Enantiomeric separation of chiral polychlorinated biphenyls on P-cyclodextrin capillary columns by means of heart-cut multidimensional gas chromatography and comprehensive two-dimensional gas chromatography applications to food samples. J. Sep. Sci. 28, 163-171. 

Glausch, A., Blanch, G.P., Schurig, V. (1996). Enantioselective analysis of chiral polychlorinated biphenyls in sediment samples by multidimensional gas chromatography-electron-capture detection after steam distillation-solvent extraction and sulfur removal. J. Chromatogr. A 723, 399 104. 

Warner, N.A., Norstrom, R.J., Wong, C.S. and Fisk, A.T. (2005) Enantiomeric fractions of chiral polychlorinated biphenyls provide insights on biotransformation capacity of Arctic biota. Environ Toxicol Chem, 24, 2763-2767. 

Figure 4.17 Correlation of Hudson River volumetric discharge at Waterford, New York, to enantiomer fractions (EFs) of dissolved (A) and particulate PCB 95 In the Hudson River Estuary. (Reproduced with permission from Environmental Science and Technology, Chiral Source Apportionment of Polychlorinated Biphenyls to the Hudson River Estuary Atmosphere and Food Web, by Brian j. Asher, Charles S. Wong and Lisa A. Rodenburg, 41(17), 6163-6169. Copyright (2007) American Chemical Society)...

Piittmann, M. Mannschreck, A. Oesch, F. Robertson, L., Chiral effects in the induction of drug-metabolizing enz3mies using synthetic atropisomers of polychlorinated biphenyls (PCBs) Biochem. Pharmacol 1989, 38, 1345-1352. 

Schurig, V Reich, S., Determination of the rotational barriers of atropisomeric polychlorinated biphenyls (PCBs) by a novel stopped-flow multidimentional gas chromatographic technique Chirality 1998, 10, 316-320. 

Haglund, R, Enantioselective separation of polychlorinated biphenyl atropisomers using chiral high-performance liquid chromatography J. Chromatogr. A 1996, 724, 219-228. 

Bordajandi, L.R. Ramos, L. Gonzalez, M.J., Chiral comprehensive two-dimensional gas chromatography with electron-capture detection applied to the analysis of chiral polychlorinated biphenyls in food samples J. Chromatogr. A 1078, 2005, 128-135. 

Reich, S. Jiminez, B. Marsih, L. Hernandez, L.M. Schurig, V Gonzalez, M.J., Congener specific determination and enantiomeric ratios of chiral polychlorinated biphenyls in striped dolphins Stenella coeruleoalba) from the Mediterranean Sea Environ. Sci. Technol. 1999, 33, 1787-1793. 

Jimenez, O. Jimenez, B. Gonzalez, M.J., Isomer-specihc polychlorinated biphenyl determination in cetaceans from the Mediterranean Sea Enantioselective occurrence of chiral polychlorinated biphenyl congeners Environ. Toxicol. Chem. 2000, 19, 2653-2660. 

Wong, C.S. Chiral polychlorinated biphenyls and their metabolites In PCBs Human and Environmental Disposition and Toxicity, L.G. Hanson L.W. Robertson, editors. University of Illinois Press Urbana IL, 2008, p. 30-50. 

Wong, C.S. Hoekstra, P.E Karlsson, H. Backus, S.M. Mabury, S.A. Muir, D.C.G., Enantiomer fractions of chiral organochlorine pesticides and polychlorinated biphenyls in Standard and Certified Reference Materials Chemosphere 2002, 49, 1339-1347. 

Garci a-Ruiz, C. Andres, R. Valera, J.L. Laborda, R Marina, M.L., Monitoring the stereoselectivity of hiodegradation of chiral polychlorinated biphenyls using electrokinetic chromatography J. Sep. Sci 2002, 25, 17-22. 

Jamshidi, A. Hunter, S. Hazrati, S. Harrad, S., Concentrations and chiral signatures of polychlorinated biphenyls in outdoor and indoor air and soil in a major U.K. conurbation Environ. Sci. Technol. 2007, 41, 2153-2158. 

Asher, B.J. Wong, C.S. Rodenburg, L.A., Chiral source apportionment of polychlorinated biphenyls to the Hudson River estuary atmosphere and food web Environ. Sci. Technol. 2007, 41, 6163-6169. 

Wong, C.S. Garrison, A.W. Smith, PD. Foreman, W.T., Enantiomeric composition of chiral polychlorinated biphenyl atropisomers in aquatic and riparian biota Environ. Sci. Technol. 2001, 35, 2448-2454. 

Chu, S. Covad, A. Van de Vijver, K. De Coen, W. Blust, R. Schepens, P, Enantiomeric signatures of chiral polychlorinated biphenyl atropisomers in livers of harbour porpoises (Phocoena phocoena) from the southern North Sea J. Environ. Monit. 2003, 5, 521-526. Chu, S. Covad, A. Haraguchi, K. Voorspoels, S. Van de Vijver K. Das, K. Bouquegneau, J.-M. De Coen, W. Blust, R. Schepens, R, Levels and enantiomeric signatures of methyl sulfonyl PCB and DDE metabolites in liver of harbor porpoises (Phocoena phocoena) from the southern North Sea Environ. Sci. TechnoL 2003, 37, 4573-4578. 

Warner, N.A. Martin, J.W. Wong, C.S., Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian c3tiochrome P-450 isozymes to form hydroxylated metabolites Environ. Sci Technol. 2009, 43, 114—121. 

Figure 8.3 Annually averaged concentrations (error bars denote I standard deviation) at outdoor sites along a rural-urban transect across Birmingham, UK (a) XPBDEs in air (pg/m ) (b) XPBDEs In soil (pg/g) (c) XPCBs In air (pg/m ) and (d) XPCBs in soils (ng/g). Soil concentrations normalized to soil organic carbon content, ((a) and (b) Reprinted with permission from Environmental Science and Technology, Concentrations of Polybrominated Diphenyl Ethers In Air and Soil on a Rural-Urban Transect Across a Major UK Conurbation, by Stuart Harrad et al., 40(15), 4548-4553. Copyright (2006) American Chemical Society, (c) and (d) Reprinted by permission from Environmental Science and Technology, Concentrations and Chiral Signatures of Polychlorinated Biphenyls In Outdoor and Indoor Air and Soil In a Major UK Conurbation, by Arsalan Jamshidi et al., 41(7), 2153-2158. Copyright (2007) American Chemical Society)...

Marina, M.L., I. Benito, J.C. Dfez-Masa, and M.J. Gonzalez. 1996. Chiral separation of polychlorinated biphenyls by micellar electrokinetic chromatography with y-cyclodextrin as modifier in the separation buffer. Chromatographia 42 269-272. 

Ramos, L., L.M. Hernandez, and M.-J. Gonzalez. 1999. Simultaneous separation of coplanar and chiral polychlorinated biphenyls by off-line pyrenyl-silica liquid chromatography and gas chromatography. Enantiomeric ratios of chiral congeners. Anal. Chem. 71 70-77. 

A.L. Crego, M.A. Garcia and M.L. Marina, Enantiomeric separation of chiral polychlorinated biphenyls by micellar electrokinetic chromatography using mixtures of bile salts and sodium dodecyl sulphate with and without gamma-cyclodextrin in the separation buffer, J. Microcolumn. Sep., 12,33-40,2000. 

C. Garcia-Ruiz, A.L. Crego and M.L. Marina, Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis. Electrophoresis, 24, 2657-2664, 2003. 

S.H. Edwards and SA. Shamsi, Chiral separation of polychlorinated biphenyls using a combination of hydroxypropyl-gamma-cyclodextrin and a polymeric chiral surfactant. Electrophoresis, 23, 1320-1327, 2002. 

Similarly, Huhnerfiiss etal. [107, 117] detected PCBs in marine and limnic biota tissues. The authors reported the presence of these xenobiotics in blue mussels (Mytilus edulis). Toxaphene pesticide was used in the southeastern US states for cotton and soya bean crops, but was subsequently banned by the EPA in 1986, due to its long persistence. Hoekstra et al. [118] collected blubber and liver samples from the bowhead whale (Balaena mysticetus) in Canada in 1997-8. The authors reported the presence of eight chiral PCB congeners (PCBs 91, 95,135,136,149,174, 176 and 183) in these samples. De Cues et al. [119] reported the presence of toxaphene, produced in large quantities similar to those of polychlorinated biphenyls. 

A few reports are available on chiral separations of pollutants using this modality of liquid chromatography. The separated chiral pollutants are 2-(2-chlorophenoxy)propionic acid and 2-(4-chlorophenoxy)propionic acid on n-alkyl-)8-D-glucopyranoside [17], ibuprofens on vancomycin [18] and PCBs on y-cyclodextrin [19]. Marina etal. [20] reported chiral separations of polychlorinated biphenyls (PCBs) 45, 84, 88, 91, 95, 132, 136, 139, 149, 171, 183 and 196 by MEKC using cyclodextrin chiral selectors. Mixtures of and y-cyclodextrins were used as chiral modifiers in a 2-(yV-cyclohexylamino)ethanesulfonic acid (CHES) buffer containing urea and sodium dodecyl sulfate (SDS) micelles. A mixture of PCBs 45, 88, 91, 95, 136, 139, 149 and 196 was separated into all 16 enantiomers in an... 

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