Physiological and molecular genetic analyses of vinyl chloride and ethene biodegradation in Nocardioides sp. strain JS614

Mattes, Timothy E.; Coleman, Nicholas V.; Spain, Jim C.; Gossett, James M.

doi:10.1007/s00203-004-0749-2

Cited by 85 publications

(137 citation statements)

References 33 publications

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“…strain JS614, Pseudomonas putida, and Ochrobactrum sp. strain TD, all of which metabolize ethene and vinyl chloride (13,14,41). EaCoMTs from these organisms share high sequence identity and similarity (Fig.…”

Section: Eacomt: Zinc-mediated Activation Of the Com Thiol Reactions mentioning

confidence: 99%

Getting a Handle on the Role of Coenzyme M in Alkene Metabolism

Krishnakumar

Sliwa

Endrizzi

et al. 2008

Microbiol Mol Biol Rev

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SUMMARY Coenzyme M (2-mercaptoethanesulfonate; CoM) is one of several atypical cofactors discovered in methanogenic archaea which participate in the biological reduction of CO2 to methane. Elegantly simple, CoM, so named for its role as a methyl carrier in all methanogenic archaea, is the smallest known organic cofactor. It was thought that this cofactor was used exclusively in methanogenesis until it was recently discovered that CoM is a key cofactor in the pathway of propylene metabolism in the gram-negative soil microorganism Xanthobacter autotrophicus Py2. A four-step pathway requiring CoM converts propylene and CO2 to acetoacetate, which feeds into central metabolism. In this process, CoM is used to activate and convert highly electrophilic epoxypropane, formed from propylene epoxidation, into a nucleophilic species that undergoes carboxylation. The unique properties of CoM provide a chemical handle for orienting compounds for site-specific redox chemistry and stereospecific catalysis. The three-dimensional structures of several of the enzymes in the pathway of propylene metabolism in defined states have been determined, providing significant insights into both the enzyme mechanisms and the role of CoM in this pathway. These studies provide the structural basis for understanding the efficacy of CoM as a handle to direct organic substrate transformations at the active sites of enzymes.

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Section: Eacomt: Zinc-mediated Activation Of the Com Thiol Reactions mentioning

confidence: 99%

Getting a Handle on the Role of Coenzyme M in Alkene Metabolism

Krishnakumar

Sliwa

Endrizzi

et al. 2008

Microbiol Mol Biol Rev

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“…As noted above, other alkene-oxidizing bacteria, specifically those that grow using ethylene and vinyl chloride as carbon sources, have been shown to use CoM for epoxide metabolism (14)(15)(16)29). For these bacteria, EaCoMT catalyzes the reaction of epoxyethane or chloroepoxyethane with CoM to form the initial products hydroxyethyl-CoM and chlorohydroxyethyl-CoM.…”

Section: Vol 188 2006 Bes Inhibition Of Bacterial Alkene Metabolismmentioning

confidence: 99%

“…1 (1,2,4,5,20,27). Recent studies of ethylene-and vinyl chloride-utilizing bacteria have shown that CoM serves as the cofactor for the utilization of these shortchain alkenes as well (14)(15)(16)29). For these strains, epoxyalkane:CoM transferase (EaCoMT) forms hydroxyethylthioether conjugates which are believed to undergo subsequent dehydrogenation and conversion to acetyl-CoA rather than carboxylation (15).…”

mentioning

confidence: 99%

Characterization of 2-Bromoethanesulfonate as a Selective Inhibitor of the Coenzyme M-Dependent Pathway and Enzymes of Bacterial Aliphatic Epoxide Metabolism

2006

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Bacterial growth with short-chain aliphatic alkenes requires coenzyme M (CoM) (2-mercaptoethanesulfonic acid), which serves as the nucleophile for activation and conversion of epoxide products formed from alkene oxidation to central metabolites. In the present work the CoM analog 2-bromoethanesulfonate (BES) was shown to be a specific inhibitor of propylene-dependent growth of and epoxypropane metabolism by Xanthobacter autotrophicus strain Py2. BES (at low [millimolar] concentrations) completely prevented growth with propylene but had no effect on growth with acetone or n-propanol. Propylene consumption by cells was largely unaffected by the presence of BES, but epoxypropane accumulated in the medium in a time-dependent fashion with BES present. The addition of BES to cells resulted in time-dependent loss of epoxypropane degradation activity that was restored upon removal of BES and addition of CoM. Exposure of cells to BES resulted in a loss of epoxypropane-dependent CO 2 fixation activity that was restored only upon synthesis of new protein. Addition of BES to cell extracts resulted in an irreversible loss of epoxide carboxylase activity that was restored by addition of purified 2-ketopropyl-CoM carboxylase/oxidoreductase (2-KPCC), the terminal enzyme of epoxide carboxylation, but not by addition of epoxyalkane:CoM transferase or 2-hydroxypropyl-CoM dehydrogenase, the enzymes which catalyze the first two reactions of epoxide carboxylation. Comparative studies of the propylene-oxidizing actinomycete Rhodococcus rhodochrous strain B276 showed that BES is an inhibitor of propylene-dependent growth in this organism as well but is not an inhibitor of CoM-independent growth with propane. These results suggest that BES inhibits propylene-dependent growth and epoxide metabolism via irreversible inactivation of the key CO 2 -fixing enzyme 2-KPCC.

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“…Plates were incubated for approximately 7 days at 30∞C with cDCE in a sealed container. Any colonies that appeared on the plates were transferred in duplicate Pathway is illustrated based on the literature cited (Arp et al, 2001;Coleman and Spain, 2003;Futagami et al, 2008;Jennings et al, 2009;Li and Wackett, 1992;Magnuson et al, 1998;Mattes et al, 2005Mattes et al, , 2010Newman et al, 1997). Anaerobic and aerobic degradation steps are represented by filled and open arrows, respectively.…”

Section: Methodsmentioning

confidence: 99%