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Evidence for a radical mechanism of the dechlorination of chlorinated propenes mediated by the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans

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Habel,  A.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Ploss,  K.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Svatos,  A.
Research Group Mass Spectrometry, MPI for Chemical Ecology, Max Planck Society;

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Boland,  W.
Department of Bioorganic Chemistry, MPI for Chemical Ecology, Max Planck Society;

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Citation

Schmitz, R., Wolf, J., Habel, A., Neumann, A., Ploss, K., Svatos, A., et al. (2007). Evidence for a radical mechanism of the dechlorination of chlorinated propenes mediated by the tetrachloroethene reductive dehalogenase of Sulfurospirillum multivorans. Environmental Science & Technology, 41(21), 7370-7375. doi:10.1021/es071026u.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0012-A32C-B
Abstract
The reductive dehalogenation of chlorinated propenes was studied with the tetrachloroethene reductive dehalogenase purified from Sulfurospirillum multivorans to obtain indications for a radical mechanism of this reaction. When reduced methyl viologen (MV), which is a radical cation, was applied as electron donor for the reduction of different chloropropenes, a significant part of MV could not be rereduced with Ti(III) citrate, indicating that a part of the MV was consumed in a side reaction. Mass spectrometric analysis of assays with MV as electron donor revealed the formation of side products, the masses of which might account for the formation of adducts from a chloropropenyl radical and reduced methyl viologen. With Ti(III) citrate as sole electron donor, 2,3-dichloropropene was reduced and as a side product, 2,5-dichloro-1,5-hexadiene was formed demonstrating that the reductive dechlorination of 2,3-dichloropropene proceeds via a radical reaction mechanism. The results support different dehalogenation mechanisms for the reductive dechlorination of chloropropenes and halogenated ethenes.