Journal article
An efficient approach to sulfate metabolites of polychlorinated biphenyls
Environment international, Vol.36(8), pp.843-848
2010
DOI: 10.1016/j.envint.2009.02.005
PMCID: PMC2939219
PMID: 19345419
Abstract
Polychlorinated biphenyls (PCBs), a major class of persistent organic pollutants, are metabolized to hydroxylated PCBs. Several hydroxylated PCBs are substrates of cytosolic phase II enzymes, such as phenol and hydroxysteroid (alcohol) sulfotransferases; however, the corresponding sulfation products have not been isolated and characterized. Here we describe a straightforward synthesis of a series of ten PCB sulfate monoesters from the corresponding hydroxylated PCBs. The hydroxylated PCBs were synthesized by coupling chlorinated benzene boronic acids with appropriate brominated (chloro-)anisoles, followed by demethylation with boron tribromide. The hydroxylated PCBs were sulfated with 2,2,2-trichloroethyl chlorosulfate using DMAP as base. Deprotection with zinc powder/ammonium formate yielded the ammonium salts of the desired PCB sulfate monoesters in good yields when the sulfated phenyl ring contained no or one chlorine substituent. However, no PCB sulfate monoesters were isolated when two chlorines were present
ortho to the sulfated hydroxyl group. To aid with future quantitative structure activity relationship studies, the structures of two 2,2,2-trichloroethyl-protected PCB sulfates were verified by X-ray diffraction.
Details
- Title: Subtitle
- An efficient approach to sulfate metabolites of polychlorinated biphenyls
- Creators
- Xueshu Li - Department of Occupational and Environmental Health, College of Public Health, University of Iowa, Iowa City, IA, 52242, USASean Parkin - Department of Chemistry, College of Arts and Sciences, University of Kentucky, Lexington, KY, 40506, USAMichael W Duffel - Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, IA, 52242, USALarry W Robertson - Department of Occupational and Environmental Health, College of Public Health, University of Iowa, Iowa City, IA, 52242, USAHans-Joachim Lehmler - Department of Occupational and Environmental Health, College of Public Health, University of Iowa, Iowa City, IA, 52242, USA
- Resource Type
- Journal article
- Publication Details
- Environment international, Vol.36(8), pp.843-848
- DOI
- 10.1016/j.envint.2009.02.005
- PMID
- 19345419
- PMCID
- PMC2939219
- NLM abbreviation
- Environ Int
- ISSN
- 0160-4120
- eISSN
- 1873-6750
- Publisher
- Elsevier Ltd
- Language
- English
- Date published
- 2010
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute; Pharmaceutical Sciences and Experimental Therapeutics; Iowa Superfund Research Program; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984001087802771
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