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PubMed2005

Asymmetrized tris(hydroxymethyl)methane as a precursor of N- and O-containing 6-membered heterocycles through ring-closing metathesis.

A novel synthetic application of asymmetrized tris(hydroxymethyl)methane (THYM), obtained in both enantiomeric forms in high e.e. via a chemoenzymatic procedure, is described. Starting from the common precursor , N- and O-containing 6-membered heterocycles have been prepared exploiting ring-closing metathesis as the key step. Possible elaborations of the double bond in and have been explored and, in the case of , conversion into the glycosidase inhibitor isofagomine has been achieved.

Cyclization↗
PubMed2005

Synthesis of mono- and geminal dimetalated carbanions of bis(phenylsulfonyl)methane using alkali metal bases and structural comparisons with lithiated bis(phenylsulfonyl)imides.

The alpha,alpha'-stabilized carbanion complexes [(PhSO2)2CHLi.THF]1, [(PhSO2)2CHNa.THF]2 and [(PhSO2)2CHK]3 were prepared by the direct deprotonation of bis(phenylsulfonyl)methane I in THF with one molar equivalent of MeLi, BuNa and BnK respectively. The geminal dianionic complexes [(PhSO2)2CLi2.THF]4, [(PhSO2)2CNa2.0.55THF]5 and [(PhSO2)2CK2]6 were similarly prepared by the reaction of I with two molar equivalents of MeLi, BuNa and BnK respectively in THF. NMR and MS solution studies of 1-3 are consistent with the formation of charge-separated species in DMSO media. Solutions studies of 4-6, in conjunction with trapping experiments, indicate that the dianions deprotonate DMSO and regenerate the monoanions 1-3. Crystallographic analysis of 1 revealed a 1D chain polymer in which the metal centers are chelated by the bis(sulfonyl) ligands and connect to neighboring units through Li-O(S) interactions. An unexpected feature of 1 is that the polymeric chains are homochiral, since the chelating ligands of the backbone adopt the same relative configuration. Also, the phenyl substituents of each chelate in 1 are oriented in a cisoid manner. The sodium derivative 2 adopts a related solid-state structure, where enantiomeric pairs of chains combine to give a 1D ribbon motif. The lithium bis(phenylsulfonyl)imides [(PhSO2)2NLi.THF]9 and [(PhSO2)2NLi.Pyr2]10 were also prepared and structurally characterized. In the solid state 9 has a similar connectivity to that found for 1 but with heterochiral chains. In comparison, the more highly solvated complex 10 forms a 1D polymeric arrangement without chelation of the ligands and with the phenyl substituents oriented in a transoid fashion.

Chelating Agents↗
PubMed1975

An improved assay for bacterial methane mono-oxygenase: some properties of the enzyme from Methylomonas methanica.

Extracts of Methylomonas methanica catalyse the O2-and NAD(P)H-dependent disappearance of bromomethane. The activity is unstable at 2 degrees C but is stable at --70 degrees C for several weeks. Bromomethane mono-oxygenase is particulate and is inhibited by metal-binding reagents, by compounds SKF 525A and Lilly 53325, by some metal ions and by acetylene. Evidence is presented that indicates that bromomethane mono-oxygenase is the enzyme responsible for methane oxidation in vivo.

Hydrogen-Ion Concentration↗
PubMed1978

Resolution of the methane mono-oxygenase of Methylococcus capsulatus (Bath) into three components. Purification and properties of component C, a flavoprotein.

1. Ion-exchange chromatography resolves the methane mono-oxygenase from soluble extracts of Methylococcus capsulatus (Bath) into three fractions. 2. Fractions A and B are comparatively stable at 0 degrees C, whereas fraction C is very unstable unless kept in the presence of sodium thioglycollate (1-10 mM) or dithiothreitol (5-10mM). 3. The active component from fraction C was purified some 80-fold. 4. Purified component C has mol. wt. 42000. Its solutions are yellow with absorption maxima at 270 and 465 nm and a shoulder at 395 nm. The 465 nm peak is abolished by reduction with NADH or sodium dithionite, or by photoreduction in the presence of EDTA. A new spectral species, probably a neutral flavin semiquinone, is observed on partial reduction of component C. 5. No copper was detected in samples of purified component C, but the protein contains 1.3-1.5 atoms of iron/molecule. 6. On boiling, component C releases a yellow-green fluorescent material that has been identified as FAD from its absorption and fluorescence spectra and by t.l.c. 7. Component C contains 1 mol of FAD/mol of protein.

Copper↗
PubMed1979

Characterization of the second prosthetic group of the flavoenzyme NADH-acceptor reductase (component C) of the methane mono-oxygenase from Methylococcus capsulatus (Bath).

1. A new two-step purification is described that routinely yields 100mg quantities of component C for biochemical studies. 2. Chemical analyses show component C purified by this procedure to contain 2 g-atoms of iron, 2 mol of acid-labile sulphide (S) and 1 mol of FAD per mol of protein. 3. The Fe-S core of component C was extruded by treating the protein with p-methoxybenzenethiol in hexamethyl phosphoramide/50mM-Tris/HCl buffer, pH 8.5 (4:1, v/v), under anaerobic conditions. The spectral properties of the extruded core suggest that component C contains 1 mol of [2Fe-2S(S-Cys)4] centre per mol of protein. 4. E.p.r. spectroscopy confirms the presence of a Fe-S centre in component C. 5. Component C catalyses the reduction by NADH of ferricyanide, 2,6-dichlorophenol-indophenol or horse heart cytochrome c, with specific activities of 50--230 units/mg of protein. 6. The optimum pH for the NADH-acceptor reductase activity is 8.5--9.0, and the apparent Km values for NADH and NADPH are 0.05mM and 15.5mM respectively. 7. Unlike methane mono-oxygenase activity, NADH-acceptor reductase activity of component C is not inhibited by 8-hydroxyquinoline or by acetylene.

Electron Spin Resonance Spectroscopy↗
PubMed2001

Evidence for anaerobic syntrophic acetate oxidation during methane production in the profundal sediment of subtropical Lake Kinneret (Israel).

Methane production was measured in samples of the profundal sediment from Lake Kinneret. Production rates of CH(4) were higher at 30 degrees C than at the in situ temperature of 15 degrees C and were higher in the top 5 cm layer than below. Turnover of [2-(14)C]-acetate resulted in the production of (14)CH(4) and (14)CO(2) with turnover times of < 42 min. However, < 30% of the added radioactivity was converted to gaseous products, indicating that only part of the acetate pool was microbially available. The calculated acetate turnover rates were sufficient to account for total CH(4) production, indicating that CH(4) was produced exclusively from acetate. This conclusion was confirmed by inhibition of methanogens with chloroform, which resulted in an almost stoichiometric accumulation of acetate. However, a large percentage (30-60%) of [2-(14)C]-acetate was converted to (14)CO(2), despite lack of reducible sulphate or other oxidants in the sediment. Anoxic preincubation of the sediment did not result in reduced production of (14)CO(2). Therefore, part of the acetate must have been oxidized rather than methanogenically cleaved. Conversion of [(14)C]-bicarbonate to (14)CH(4) indicated that 30-50% of total CH(4) production originated from reduction of CO(2). To reconcile the relatively high contribution of H(2)/CO(2)-dependent methanogenesis with the relatively high oxidative conversion of acetate, we assume that part of the acetate was used syntrophically by consortia of acetate-oxidizing bacteria and H(2)/CO(2)-using methanogens. This conclusion is supported by favourable thermodynamic conditions for syntrophic acetate oxidation under in situ conditions and complete inhibition of [2-(14)C]-acetate turnover at high H(2) partial pressures. Further evidence to support this conclusion comes from the analysis of the structure of the archaeal community. Terminal restriction fragment length polymorphism (T-RFLP) and partial sequence analysis of the SSU rRNA genes amplified from DNA extracts of the sediment showed Methanomicrobiaceae as the dominant methanogenic group, whereas acetoclastic methanogens could not be detected.

Acetates↗
PubMed1988

Physiological importance of the heterodisulfide of coenzyme M and 7-mercaptoheptanoylthreonine phosphate in the reduction of carbon dioxide to methane in Methanobacterium.

The heterodisulfide of the two coenzymes 2-mercaptoethanesulfonic acid (coenzyme M, HS-CoM) and N-(7-mercaptoheptanoyl)threonine O3-phosphate (HS-HTP) increased the rate of CO2 reduction to methane by cell extracts 42-fold. The stimulation resulted from activation of the initial step of methanogenesis, the production of formylmethanofuran from methanofuran and CO2. These results establish a role for this heterodisulfide (CoM-S-S-HTP) in the reduction of CO2 to formylmethanofuran. Evidence indicates that CoM-S-S-HTP is the labile intermediate that accounts for the coupling of the reduction of 2-(methylthio)ethanesulfonic acid by the methylreductase to formylmethanofuran biosynthesis, the "RPG effect." The heterodisulfide was found to be labile in cell extracts due to enzyme-catalyzed reduction and possibly thioldisulfide exchange.

Carbon Dioxide↗
PubMed2000

Oxygen kinetic isotope effects in soluble methane monooxygenase.

Soluble methane monooxygenase (sMMO) contains a nonheme, carboxylate-bridged diiron site that activates dioxygen in the catalytic oxidation of hydrocarbon substrates. Oxygen kinetic isotope effects (KIEs) have been determined under steady-state conditions for the sMMO-catalyzed oxidation of CH(3)CN, a liquid substrate analog. Kinetic studies of the steady-state sMMO reaction revealed a competition between fully coupled oxygenase activity, which produced glycolonitrile (HOCH(2)CN) and uncoupled oxidase activity that led to water formation. The oxygen KIE was measured independently for both the oxygenase and oxidase reactions, and values of 1.0152 +/- 0.0007 and 1.0167 +/- 0.0010 were obtained, respectively. The isotope effects and separate dioxygen binding studies do not support irreversible formation of an enzyme-dioxygen Michaelis complex. Additional mechanistic implications are discussed in the context of previous data obtained from single turnover and steady-state kinetic studies.

Kinetics↗
PubMed2005

Activation of Nur77 by selected 1,1-Bis(3'-indolyl)-1-(p-substituted phenyl)methanes induces apoptosis through nuclear pathways.

Nur77 is an orphan receptor and a member of the nerve growth factor-I-B subfamily of the nuclear receptor family of transcription factors. Based on the results of transactivation assays in pancreatic and other cancer cell lines, we have now identified for the first time Nur77 agonists typified by 1,1-bis(3-indolyl)-1-(p-anisyl)methane that activate GAL4-Nur77 chimeras expressing wild-type and the ligand binding domain (E/F) of Nur77. In Panc-28 pancreatic cancer cells, Nur77 agonists activate the nuclear receptor, and downstream responses include decreased cell survival and induction of cell death pathways, including tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) and poly(ADP-ribose) polymerase (PARP) cleavage. Moreover, the transactivation and apoptotic responses are also induced in other pancreatic, prostate, and breast cancer cells that express Nur77. In Panc-28 cells, small inhibitory RNA for Nur77 reverses ligand-dependent transactivation and induction of TRAIL and PARP cleavage. Nur77 agonists also inhibit tumor growth in vivo in athymic mice bearing Panc-28 cell xenografts. These results identify compounds that activate Nur77 through the ligand binding domain and show that ligand-dependent activation of Nur77 through nuclear pathways in cancer cells induces cell death and these compounds are a novel class of anticancer agents.

Active Transport, Cell Nucleus↗
PubMed2002

Diversity of the particulate methane monooxygenase gene in methanotrophic samples from different rice field soils in China and the Philippines.

Methanotrophic bacteria play a crucial role in regulating the emission of CH4 from rice fields into the atmosphere. We investigated the CH4 oxidation activity together with the diversity of methanotrophic bacteria in ten rice field soils from different geographic locations. Upon incubation of aerated soil slurries under 7% CH4, rates of CH4 oxidation increased after a lag phase of 1-4 days and reached values of 3-10 micromol d(-1) g-dw(-1) soil. The methanotrophic community was assayed by retrieval of the pmoA gene which encodes the a subunit of the particulate methane monooxygenase. After extraction of DNA from actively CH4-oxidizing soil samples and PCR-amplification of the pmoA, the community was analyzed by Denaturant Gradient Gel Electrophoresis (DGGE) and Terminal Restriction Fragment Length Polymorphism (T-RFLP). DGGE bands were excised, the pmoA re-amplified, sequenced and the encoded amino acid sequence comparatively analyzed by phylogenetic treeing. The analyses allowed the detection of pmoA sequences related to the following methanotrophic genera: the type-I methanotrophs Methylobacter, Methylomicrobium, Methylococcus and Methylocaldum, and the type-II methanotrophs Methylocystis and Methylosinus. T-RFLP analysis detected a similar diversity, but type-II pmoA more frequently than DGGE. All soils but one contained type-II in addition to type-I methanotrophs. Type-I Methylomonas was not detected at all. Different combinations of methanotrophic genera were detected in the different soils. However, there was no obvious geographic pattern of the distribution of methanotrophs.

Agriculture↗
PubMed1984

Methane formation in faunated and ciliate-free cattle and its relationship with rumen volatile fatty acid proportions.

Twelve steers fitted with rumen cannulas were used in three separate experiments to investigate the effects of the presence or absence of rumen ciliate protozoa on methane production. The diet consisted of 850 g barley and 150 g protein supplement/kg, and was given in three feeds daily at a restricted level of 61 g/kg live weight 0.75. Animals were defaunated initially by allowing ad lib. consumption of this diet and were then maintained ciliate-free by isolation or were faunated by inoculation with a mixed ciliate suspension. Samples of rumen fluid were taken routinely for the assessment of microbial populations and for volatile fatty acid (VFA) analysis and energy and nitrogen balances and digestibility measurements were made at intervals while animals were confined in respiration chambers. In each experiment the rumen VFA proportions changed from a high-propionate pattern under ciliate-free conditions to a low-propionate, high-butyrate pattern in the presence of ciliates: differences between treatments were highly significant (P less than 0.001). There were also marked differences between treatments in CH4 production but a reliable comparison was possible only in Expt 3, in which CH4 was significantly higher (P less than 0.001) in the presence of a rumen ciliate population. In Expt 3 the increased loss of energy as CH4 in the faunated animals amounted to 4.8 MJ/100 MJ energy intake. Stoichiometric estimates of CH4 production derived from the observed VFA proportions showed good agreement with CH4 production as measured in respiration chambers. On average, the stoichiometric CH4 values overestimated CH4 production by a factor of 1.08. Highly significant linear relationships (P less than 0.001) were observed between the molar proportion of each major VFA and the quantity of CH4 produced: the proportion of propionic acid was inversely related to CH4 and showed the lowest residual standard deviation of all the relationships examined. The losses of energy in faeces and urine did not differ between treatments hence the increased loss of energy as CH4 in the faunated animals resulted in a significant reduction in the metabolizability of the diet from 0.73 to 0.69 (P less than 0.05). No significant differences were detected between treatments in heat production, apparent digestibility coefficients or N balance. It is suggested that the rumen ciliates, by modifying the rumen VFA proportions, are directly responsible for the increased CH4 production in faunated animals.

Animals↗
PubMed1986

The significance of carbon dioxide and methane measurements in the estimation of heat production in cattle.

1. Records of metabolic measurements on cattle by open-circuit indirect calorimetry have been examined to determine the practical significance in the calculation of heat production of including measurements of carbon dioxide and methane in addition to the measurement of oxygen. 2. It was found that the combined effects of CO2 and CH4 made only a small contribution to the total estimation of heat production which could be calculated with approximately +/- 1% accuracy from analysis of O2 alone.

Animals↗
PubMed1987

Methane excretion in the growing pig.

Total methane excretion (CH4 in breath + flatus) was measured in two experiments with thirty-six castrated male pigs (Danish Landrace) during the growth period from 20 to 120 kg live weight (LW). In Expt A, twenty-eight pigs were fed on a commercial diet alternately at high (HFL; metabolizable energy (ME) 1234 (SE 41) kJ/kg LW 0.75) or low (LFL; ME 784 (SE 31) kJ/kg LW 0.75) feed levels in different weight classes. In Expt B, eight pigs were constantly fed on a semi-purified diet at HFL without (-oil) or with 90 g soya-bean oil/kg diet (+oil) corresponding to daily intakes of ME of 1339 (SE 11) and 1413 (SE 8) kJ/kg LW 0.75 respectively. CH4 excretion was measured during 24 h respiration trials in open-air-circulation chambers. About 1 litre CH4 was excreted per day at 20-25 kg LW increasing to a maximum of 12 litres at 120 kg LW, which corresponded to no more than 1.2% of dietary gross energy. In Expt A, CH4 excretion increased linearly with LW, while in Expt B the increase was linear until about 70 kg LW, when it reached a plateau. On average LFL reduced CH4 excretion by 23% compared with HFL. When related to dry matter (DM) intake, however, the pigs on LFL excreted 3.1 litres CH4/kg dietary DM and those on HFL 2.5 litres CH4/kg dietary DM, the difference being significant (P less than 0.05). In Expt B the inclusion of soya-bean oil in the basal diet (+oil) reduced CH4 excretion by 26% compared with the diet without oil (-oil).(ABSTRACT TRUNCATED AT 250 WORDS)

Animal Nutritional Physiological Phenomena↗
PubMed2002

Rumen fermentation and nitrogen balance of lambs fed diets containing plant extracts rich in tannins and saponins, and associated emissions of nitrogen and methane.

Tannins were added to experimental diets at levels of 1 and 2 g/kg DM (hydrolysable tannins; Castanea sativa wood extract) and saponins at 2 and 30 mg/kg DM (sarsaponin; Yucca schidigera extract). These levels were far below thresholds expected to be adverse in ruminants. Effects were measured in lambs by comparison with unsupplemented control diets calculated to be either deficient (10%) or adequate in protein. The diets consisted of hay, concentrate (1:1) and extra wheat starch with increasing body weight. Ruminal pH, VFA concentration, protozoa count and apparent digestibilities of organic matter and fibre did not differ among treatments. The low tannin dose significantly decreased bacteria count compared to the high saponin dose. Saponin supplementation and the high tannin dose showed some potential to reduce ruminal ammonia concentration. This was associated with weak trends towards lower urine N excretion (only tannins) and ammonia emission from manure. Methane release was increased by the low tannin dose compared to the unsupplemented control. Diet effects on heat production were not systematic. In conclusion, the extracts rich in tannins or saponins gave only slight indications for either increased body nitrogen retention or reduced nitrogen emission. However, effects might have been larger with more pronounced dietary protein deficit.

Animal Feed↗
PubMed2005

Oxidation of 13C-labeled methane in surface crusts of pig- and cattle slurry.

Storage tanks for slurry from animal production constitute important point sources for emission of CH4 into the atmosphere. Recent investigations have demonstrated that surface crust formed on top of animal slurry provides a habitat for CH4 oxidation activity, a finding which may open for new opportunities to reduce greenhouse gas emissions during storage of animal wastes. In this work, 13C-labeled CH4 was used as a tracer to examine the absolute rates of CH4 oxidation and production in intact crust materials, collected from six different pig- and cattle slurry tanks in late autumn. Methane concentrations were generally reduced in the presence of surface crust samples, with the exception of a LECA-based (light expanded clay aggregates) crust from a pig slurry tank. In four samples, CH4 consumption was induced following a 2-4 days lag phase, whereas one cattle slurry crust consumed CH4 immediately and showed a 92% decline in CH4 concentration within the first week. Consumption of 13C-labeled CH4 was paralleled by the production of 13C-labeled CO2, thus providing direct evidence that microbial oxidation of CH4 to CO2 was taking place. Between 23% and 36% of the CH4-13C consumed in the active samples was accounted for in the gas phase CO2 indicating incomplete conversion of CH4 to CO2; however, comparable amounts of 13C was immobilized in the crust samples. Overall, the results showed that significant CH4 oxidation to CO2 in slurry crust samples occurs immediately or is inducible upon exposure to CH4.

Air Pollutants↗