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3 protocols using pcb 204

1

Synthesis and Characterization of Halogenated Biphenyl Metabolites

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PCB 136, 2,2′,3,3′,6,6′-hexachlorobiphenyl-4-ol (4-136), 2,2′,3,3′,6,6′-hexachlorobiphenyl-5-ol (5-136), 4,5-dimethoxy-2,2′,3,3′,6,6′-hexachlorobiphenyl (methylated derivative of 2,2′,3,3′,6,6′-hexachlorobiphenyl-4,5-diol; 4,5-136) and 2,2′,3′,4,6,6′-hexachloro-3-methoxybiphenyl (methylated derivative of 2,2′,3′,4,6,6′-hexachlorobiphenyl-3-ol; 3-150) were synthesized as described previously (Waller et al. 1999 (link)). The chemical structures and the abbreviations of the HO-PCB metabolites are shown in Figure 1A. Surrogate recovery standards (2,3,4′,5,6-pentachlorobiphenyl, PCB 117; 2′,3,3′,4,5,5′-hexachlorobiphenyl-4-ol, 4-159) and internal standard (2,2′,3,4,4′,5,6,6′-octachlorobiphenyl, PCB 204) were purchased from Accustandard (New Haven, CT). NAC and tetrabutylammonium sulfite were purchased from Fisher Scientific (Pittsburg, PA, USA). L-Glutathione and β-nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate (NADPH) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Pesticide grade n-hexane, 2-propanol and methyl tert-butyl ether (MTBE) were purchased from Fisher Scientific (Pittsburg, PA, USA).
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2

Synthesis and Separation of PCB 136 Atropisomers

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Dimethyl sulfoxide (DMSO), sodium phosphate
dibasic (Na2HPO4), sodium phosphate monobasic
(NaH2PO4), magnesium chloride (MgCl2), tetrabutylammonium sulfite, sodium sulfite, and pesticide grade
solvents were obtained from Fisher Scientific (Pittsburgh, PA, USA).
Nicotinamide adenine dinucleotide phosphate reduced (NADPH) was purchased
from Sigma-Aldrich Co. (St. Louis, MO, USA). Racemic PCB 136 was synthesized
by the Ullmann coupling of 2,3,6-trichloro-1-iodobenzene,28 and the atropisomers of PCB 136 were separated
using two serially connected Nucleodex β-PM columns (Macherey-Nagel,
Düren, Germany). The enantiomeric fractions (EF = Area(+)-PCB 136 /(Area(+)-PCB 136 + Area(−)-PCB 136)) of (−)-PCB
136 and (+)-PCB 136 were 0.01 and 1.00, respectively.27 (link) 2,2′,3,3′,6,6′-Hexachlorobiphenyl-4-ol
(4–136), 2,2′,3,3′,6,6′-hexachlorobiphenyl-5-ol
(5–136), 4,5-dimethoxy-2,2′,3,3′,6,6′-hexachlorobiphenyl,
and 2,2′,3′,4,6,6′-hexachloro-3-methoxybiphenyl
were prepared as described elsewhere.29 (link) Recovery standards (2,3,4,4′,5,6-hexachlorobiphenyl, PCB
166; 2,3,4′,5,6-pentachlorobiphenyl, PCB 117; 2,3,3′,4,5,5′-hexachlorobiphenyl-4-ol,
4′-159) and the internal standard (2,2′,3,4,4′,5,6,6′-octachlorobiphenyl,
PCB 204) were purchased from Accustandard (New Haven, CT).
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3

Comprehensive PCB Standard Solution Composition

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Details of
PCB standard solution
can be found in Table S1. Briefly, the
PCB standard solution was composed of (i) 209 PCB congeners (AccuStandard,
New Haven, CT, USA); (ii) 10 13C-PCB surrogate standards
(mono- to deca-chlorinated; Wellington Laboratories, Guelph, ON, Canada);
and (iii) d5-PCB30 (Cambridge Isotope Laboratories, Andover,
MA, USA), which is used as an internal standard together with PCB204
(AccuStandard). PCB congener names are in accordance with the United
States Environmental Protection Agency (US EPA).44
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