Trichloroethylene oxide

Henry SM, Grbic-Galic D. 1991a. Influence of endogenous and exogenous electron donors and trichloroethylene oxidation toxicity on trichloroethylene oxidation by methanotrophic cultures from a groundwater aquifer. Appl Environ Microbiol 57 236-244. 

Miller RE, Guengerich FP. 1982. Oxidation of trichloroethylene by liver microsomal cytochrome P-450 Evidence for chlorine migration in a transition state not involving trichloroethylene oxide. Biochemistry 21 1090-1097. 

Uehleke H, Poplawski-Tabarelli S, Bonse G, et al. 1977. Spectral evidence for 2,2,3-trichloro-oxirane formation during microsomal trichloroethylene oxidation. Arch Toxicol 37 95-105. 

Shang TQ, SL Doty, AM Wilson, WN Howald, MP Goprdon (2001) Trichloroethylene oxidative metabolism in plants the trichloroethanol pathway. Phytochemistry 58 1055-1065. 

Henry SM, D Grbic-Galic (1991) Inhibition of trichloroethylene oxidation by the transformation intermediate carbon monoxide. Appl Environ Microbiol 57 1770-1776. 

Newman LM, LP Wackett (1991) Fate of 2,2,2-trichloroacetaldehyde (chloral hydrate) produced during trichloroethylene oxidation by methanotrophs. Appl Environ Microbiol 57 2399-2402. 

Trichloroethylene oxide (trichlorooxirane, 10.89, Fig. 10.22) has received particular attention due to its toxicological significance and the widespread use of its parent compound trichloroethylene (10.87) [153] [155]. Chloral... 

Fig. 10.22. Simplified reactivity and metabolism of trichloroethylene (10.87) to chloral (10.88) and to trichloroethylene oxide (10.89), followed by rearrangement reactions and/or hydrolysis...

R. E. Miller, F. P. Guengerich, Oxidation of Trichloroethylene by Liver Microsomal Cytochrome P450 Evidence for Chloride Migration in a Transition State not Involving Trichloroethylene Oxide , Biochemistry 1982, 21, 1090 - 1097. 

H. Cai, F. P. Guengerich, Acylation of Protein Lysines by Trichloroethylene Oxide , Chem. Res. Toxicol. 2000,13, 327 - 335 H. Cai, F. P. Guengerich, Reaction of Trichloroethylene and Trichloroethylene Oxide with Cytochrome P450 Enzymes Inactivation and Sites of Modification , Chem. Res. Toxicol. 2001, 14, 451 - 458. 

Shang TQ, Doty SL, Wilson AM, Howald WN, Gordon MP (2001) Trichloroethylene Oxidative Metabolism in Plants The Trichloroethanol Pathway. Phytochemistry 58 1055... 

Brusseau GA, Tsien HC, Hanson RS, Wackett LP (1990) Optimization of trichloroethylene oxidation by methanotrophs and the sue of a colorimetric assay to detect soluble methane monooxygenase activity. Biodegrad 1, 19-29. 

The metabolism of trichloroethylene has been the subject of several reviews (3, 38, 196, 217, 255, 471). Trichloroethylene was shown to be metabolically activated via epoxidation of its olefinic bond. The formation of trichloroethylene oxide in the presence of liver microsomes was determined by spectral studies of the cytochrome P-450 complex (465, 466). The identification of chloral as an in vitro metabolite (61, 403) and of trichloromethanol and trichloroacetic acid as in vivo metabolites in rats (94) and dogs (60) supports the metabolic activation pathway outlined in Fig. 20. 

Although most olefin oxidations appear to proceed via a synchronous mechanism to give the epoxides, strong experimental evidence for the oxidation of at least some olefinic bonds via a nonconcerted mechanism is provided by the occasional direct formation of carbonyl rather than epoxide products. Early work showed that trichloroethylene is oxidized to both trichloroethylene oxide and trichloroacetaldehyde [174, 175], The demonstration that trichloroacetaldehyde did not derive from trichloroethylene oxide under the experimental conditions required that the two products be formed by distinct mecha-... 

Kawi S, Te M. MCM-48 Supported Chromium Catalyst for Trichloroethylene Oxidation. Catal Today 1998 44 101-109. 

DiSpirito, A.A, Gulledge, J, Shiemke, A.K, Murrell, IC, Lidstrom, M E., Krema, C.L. 1991/1992. Trichloroethylene oxidation by the membrane-associated methane monooxygenase in type I, type n and type X methanotrophs. Biodegradation 2(3) 151-164. 

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