1,4-Dioxane
1,4-Dioxane is used as a stabilizer in chlorinated solvents. It is an emerging water contaminant known to cause respiratory tract and eye irritant. Furthermore, it is considered a possible human carcinogen, having been shown to be one in rats and guinea pigs. The main routes of human exposure are dermal contact, ingestion, and inhalation ([http://www.ncbi.nlm.nih.gov/pubmed/8713712|DeRosa et al., 1996]). Both P. dioxanivorans CB1190 and P. benzenivorans B5 contain putative dioxane monooxygenases induced by 1,4-dioxane or THF. Other strains are capable of cometabolic degradation after growth on THF, propane, and toluene. Based on intermediates identified during degradation, 1,4-dioxane is likely hydroxylated at an ether-bond-associated carbon atom by monooxygenases, resulting in spontaneous oxidizion and ring cleavage to form 2-hydroxyethoxyacetate. A second monooxygenase attack at either the ortho or para position with respect to the carboxylic acid moiety yields a mixture of two dihydroxyethoxyacetates. Spontaneous protonation of the hemiacetal bond results in the progressive formation of various small organic molecules including ethylene gylcol, glyoxylate, glycoaldehyde, oxalate (not shown), and glycolate ([http://www.ncbi.nlm.nih.gov/pubmed/18044507|Mahendra et al., 2007]). The fungus Cordyceps sinensis is able to use 1,4-Dioxane as a sole source of carbon. 1,4-Dioxane is converted to two molecules of ethylene glycol via the proposed formation of two hemiacetals at one side of the dioxane molecule by etherase-type reactions ([http://www.ncbi.nlm.nih.gov/pubmed/15746326|Nakamiya et al., 2005]). Ethylene glycol is degraded via intermediary metabolism. Extracellular fungal peroxygenases have also been shown to oxidatively cleave a diverse set of low molecular weight ethers including 1,4-dioxane ([http://www.ncbi.nlm.nih.gov/pubmed/19713216|Kinne et al., 2009]).