title: Ozone-Activated Halogenation of Mono- and Dimethylbipyrrole in Seawater.
abstract: Polyhalogenated N-methylbipyrroles of two different structure classes have been detected worldwide in over 100 environmental samples including seawater, bird eggs, fish, dolphin blubber, and in the breast milk of humans that consume seafood. These molecules are concentrated in the fatty tissues in comparable abundance to some of the most important anthropogenic contaminants, such as the halogenated flame-retardants and pesticides. Although the origin of these compounds is still unknown, we present evidence that the production of these materials can involve the direct ozone activated seawater halogenation of N-methylbipyrrole precursors. This observation shows that environmental polyhalogenated bipyrroles can be produced via an abiotic process, and implies that the ozone activated halogenation of a variety of natural and anthropogenic seawater organics may be a significant process occurring in surface ocean waters.
authors.affiliation: Scripps Center for Oceans and Human Health, ‡Center for Marine Biotechnology and Biomedicine, §Geoscience Research Division, Scripps Institution of Oceanography, University of California at San Diego , La Jolla, California 92093, United States.
authors.forename: Abdhesh
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Scripps Center for Oceans and Human Health, ‡Center for Marine Biotechnology and Biomedicine, §Geoscience Research Division, Scripps Institution of Oceanography, University of California at San Diego , La Jolla, California 92093, United States.
authors.forename: Miles
authors.initials: M
authors.lastname: Borgen
authors.affiliation: Scripps Center for Oceans and Human Health, ‡Center for Marine Biotechnology and Biomedicine, §Geoscience Research Division, Scripps Institution of Oceanography, University of California at San Diego , La Jolla, California 92093, United States.
authors.forename: Lihini I
authors.initials: LI
authors.lastname: Aluwihare
authors.affiliation: Scripps Center for Oceans and Human Health, ‡Center for Marine Biotechnology and Biomedicine, §Geoscience Research Division, Scripps Institution of Oceanography, University of California at San Diego , La Jolla, California 92093, United States.
authors.forename: William
authors.identifier: 0000-0002-8955-1735
authors.initials: W
authors.lastname: Fenical
mesh_terms: D004784:Environmental Monitoring; D005411:Flame Retardants; D054879:Halogenation; D010126:Ozone; D012623:Seawater / Q000737:chemistry; D014874:Water Pollutants, Chemical
chemical_list: D005411:Flame Retardants; D014874:Water Pollutants, Chemical; D010126:Ozone