Characterization of intermediates in the microbial desulfurization of dibenzothiophene

Olson, Edwin S.; Stanley, Daniel C.; Gallagher, John

doi:10.1021/ef00037a025

Cited by 78 publications

(49 citation statements)

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“…Benzothiophene S,S-dioxide (BTHO,) ; molecular ion peak at m/e = 166; fragment-ion peaks at m/e = 150 and m/e = 134, consistent with the loss of 0 and 2 0 , respectively, from the molecular ion peak (Fig. 3f) peaks are also consistent with the identity of this species as BTHO,, given that this molecule may convert to either of two isomeric sultine species, under electronimpact, prior to fragmentation (Bowie et al, 1966;Fields & Meyerson, 1966;Olson et al, 1993). As shown in Fig.…”

Section: Peak (D)supporting

confidence: 55%

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Isolation of a unique benzothiophene-desulphurizing bacterium, Gordona sp. strain 213E (NCIMB 40816), and characterization of the desulphurization pathway

Gilbert¹,

Morton²,

Buchanan³

et al. 1998

Microbiology

107

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Gordona sp. strain 213E (NCIMB 40816) grew in pure culture in a mineral salts medium containing fructose as a source of carbon and energy, and benzothiophene (BTH) as the sole source of sulphur. During growth a phenolic compound accumulated, as indicated by the production of a blue colour on addition of Gibb's reagent. Therefore this pathway is analogous to the dibenzothiophene (DBT) desulphurization pathway of Rhodococcus sp. strain IGTS8, in which 2-hydroxybiphenyl accumulates during growth with DBT as the sole sulphur source. Ethyl acetate extraction of the culture medium yielded the metabolites benzothiophene S-oxide (BTHO), benzothiophene S,S-dioxide (BTHO2), benzo[c][1,2]oxathiin 6-oxide (BcOTO), 2-(2'-hydroxyphenyl)ethan 1-al (HPEal) and benzofuran (BFU). The deduced pathway for BTH desulphurization is BTH ? BTHO ? BTHO2 ? HPESi- ? HPEal. HPESi- is (Z)-2-(2'-hydroxyphenyl)ethen 1-sulphinate, the stable aqueous-solution form of BcOTO. It was concluded that HPEal was the Gibb's-reagent-reactive phenolic compound which accumulated in the culture medium of strain 213E during growth, and that the presence of BFU was due to partial condensation of HPEal during the ethyl acetate extraction procedure. Gordona sp. strain 213E was unable to grow in a mineral salts medium containing fructose as a source of carbon and energy and DBT as the sole sulphur source. BTH-desulphurization-active cells (grown using BTH as sole sulphur source) were unable to desulphurize DBT. Likewise Rhodococcus sp. strain IGTS8 was unable to grow using BTH as the sole sulphur source, and DBT-desulphurization-active cells of strain IGTS8 (grown using DBT as sole sulphur source) were unable to desulphurize BTH. This absence of cross-reactivity is discussed in terms of fundamental differences in the chemistry of the DBT- and BTH-desulphurization reactions.

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Section: Peak (D)supporting

confidence: 55%

“…strain IGTS8 and in Escherichia coli. The operon has been cloned and sequenced (Denome et al, 1993(Denome et al, ,1994 and the metabolic pathway has been elucidated (Olson et al, 1993;Oldfield et al, 1997). The enzymes have been purified and partially characterized (Lei & Tu, 1996;Gray et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Isolation of a unique benzothiophene-desulphurizing bacterium, Gordona sp. strain 213E (NCIMB 40816), and characterization of the desulphurization pathway

Gilbert¹,

Morton²,

Buchanan³

et al. 1998

Microbiology

107

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“…strain IGTS8 was isolated from a mixed culture obtained from a sulfur-limited continous-culture system capable of using organically bound sulfur (293,434,469). Strain IGTS8 converts DBT to dibenzothiophene-5-oxide (DBTO), then to dibenzene-5,5-dioxide (DBTO 2 ), then to 2-(2-hydroxybiphenyl)-benzenesulfinate (HPBS), and finally to 2-hydroxybiphenyl (HBP) to release inorganic sulfur (464,465) in a pathway involving two monooxygenases and a desulfinase (224). This enzyme system also transforms alkyl-and arylsubstituted DBT (373).…”

Section: Microbial Desulfurizationmentioning

confidence: 99%

Recent Advances in Petroleum Microbiology

Hamme¹,

Singh

Ward

2003

Microbiol Mol Biol Rev

1,201

640

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Recent advances in molecular biology have extended our understanding of the metabolic processes related to microbial transformation of petroleum hydrocarbons. The physiological responses of microorganisms to the presence of hydrocarbons, including cell surface alterations and adaptive mechanisms for uptake and efflux of these substrates, have been characterized. New molecular techniques have enhanced our ability to investigate the dynamics of microbial communities in petroleum-impacted ecosystems. By establishing conditions which maximize rates and extents of microbial growth, hydrocarbon access, and transformation, highly accelerated and bioreactor-based petroleum waste degradation processes have been implemented. Biofilters capable of removing and biodegrading volatile petroleum contaminants in air streams with short substrate-microbe contact times (<60 s) are being used effectively. Microbes are being injected into partially spent petroleum reservoirs to enhance oil recovery. However, these microbial processes have not exhibited consistent and effective performance, primarily because of our inability to control conditions in the subsurface environment. Microbes may be exploited to break stable oilfield emulsions to produce pipeline quality oil. There is interest in replacing physical oil desulfurization processes with biodesulfurization methods through promotion of selective sulfur removal without degradation of associated carbon moieties. However, since microbes require an environment containing some water, a two-phase oil-water system must be established to optimize contact between the microbes and the hydrocarbon, and such an emulsion is not easily created with viscous crude oil. This challenge may be circumvented by application of the technology to more refined gasoline and diesel substrates, where aqueous-hydrocarbon emulsions are more easily generated. Molecular approaches are being used to broaden the substrate specificity and increase the rates and extents of desulfurization. Bacterial processes are being commercialized for removal of H2S and sulfoxides from petrochemical waste streams. Microbes also have potential for use in removal of nitrogen from crude oil leading to reduced nitric oxide emissions provided that technical problems similar to those experienced in biodesulfurization can be solved. Enzymes are being exploited to produce added-value products from petroleum substrates, and bacterial biosensors are being used to analyze petroleum-contaminated environments

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“…We have also isolated Bacillus subtilis WU-S2B (9) and Mycobacterium phlei WU-F1 (2), which could desulfurize DBT and its derivatives over a wide temperature range of 20 to 50°C and at the highest level at 45 to 50°C. These bacteria desulfurize DBT through the sulfur-specific degradation pathway with the selective cleavage of carbon-sulfur (C-S) bonds without reducing the energy content (4,21,22). Naphtho[2,1-b]thiophene (NTH) (see Fig.…”

mentioning

confidence: 99%

“…Some mesophilic and thermophilic DBT-desulfurizing microorganisms have been isolated, for example, Rhodococcus sp. strain IGTS8 (1,4,21,22), Rhodococcus erythropolis D-1 (8), R. erythropolis H-2 (17,18), R. erythropolis KA2-5-1 (6), and Paenibacillus sp. strain A11-2, which desulfurizes DBT at 60°C (7,11).…”

mentioning

confidence: 99%

Biodesulfurization of Naphthothiophene and Benzothiophene through Selective Cleavage of Carbon-Sulfur Bonds by Rhodococcus sp. Strain WU-K2R

Kirimura

Furuya

Sato

et al. 2002

Appl Environ Microbiol

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Naphtho[2,1-b]thiophene (NTH) is an asymmetric structural isomer of dibenzothiophene (DBT), and in addition to DBT derivatives, NTH derivatives can also be detected in diesel oil following hydrodesulfurization treatment. Rhodococcus sp. strain WU-K2R was newly isolated from soil for its ability to grow in a medium with NTH as the sole source of sulfur, and growing cells of WU-K2R degraded 0.27 mM NTH within 7 days. WU-K2R could also grow in the medium with NTH sulfone, benzothiophene (BTH), 3-methyl-BTH, or 5-methyl-BTH as the sole source of sulfur but could not utilize DBT, DBT sulfone, or 4,6-dimethyl-DBT. On the other hand, WU-K2R did not utilize NTH or BTH as the sole source of carbon. By gas chromatography-mass spectrometry analysis, desulfurized NTH metabolites were identified as NTH sulfone, 2-hydroxynaphthylethene, and naphtho Sulfur oxides generated by combustion of fossil fuel lead to acid rain and air pollution. Therefore, today petroleum is treated by hydrodesulfurization (HDS) using metallic catalysts in the presence of hydrogen gas under extremely high temperature and pressure. Although HDS can remove various types of sulfur compounds, some types of heterocyclic sulfur compounds cannot be removed. Dibenzothiophene (DBT) is one such recalcitrant organosulfur compound and is widely recognized as a model target compound for deeper desulfurization, since DBT derivatives can be detected in diesel oil following HDS treatment. Therefore, the application of a biodesulfurization process using a DBT-desulfurizing microorganism following HDS, mainly for diesel oil, has attracted attention for achievement of deeper desulfurization (16,20). Some mesophilic and thermophilic DBT-desulfurizing microorganisms have been isolated, for example, Rhodococcus sp. strain IGTS8 (1, 4, 21, 22), Rhodococcus erythropolis D-1 (8), R. erythropolis H-2 (17, 18), R. erythropolis KA2-5-1 (6), and Paenibacillus sp. strain A11-2, which desulfurizes DBT at 60°C (7, 11). We have also isolated Bacillus subtilis WU-S2B (9) and Mycobacterium phlei WU-F1 (2), which could desulfurize DBT and its derivatives over a wide temperature range of 20 to 50°C and at the highest level at 45 to 50°C. These bacteria desulfurize DBT through the sulfur-specific degradation pathway with the selective cleavage of carbon-sulfur (C-S) bonds without reducing the energy content (4,21,22). Naphtho[2,1-b]thiophene (NTH) (see Fig. 3B), which includes a benzothiophene (BTH) (see Fig. 3A) structure, is an asymmetric structural isomer of DBT. Recently it has become apparent that in addition to DBT derivatives, NTH derivatives can also be detected in diesel oil following HDS treatment, although NTH derivatives are minor components in comparison with DBT derivatives (unpublished data). Therefore, NTH may also be a model target compound for deeper desulfurization. Kropp et al. (13) have reported that Pseudomonas sp. strain W1 could degrade NTH. However, this bacterium utilized NTH as the carbon source with reducing the energy content, and the sulfur atom was not remo...

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Characterization of intermediates in the microbial desulfurization of dibenzothiophene

Cited by 78 publications

References 0 publications

Isolation of a unique benzothiophene-desulphurizing bacterium, Gordona sp. strain 213E (NCIMB 40816), and characterization of the desulphurization pathway

Isolation of a unique benzothiophene-desulphurizing bacterium, Gordona sp. strain 213E (NCIMB 40816), and characterization of the desulphurization pathway

Recent Advances in Petroleum Microbiology

Biodesulfurization of Naphthothiophene and Benzothiophene through Selective Cleavage of Carbon-Sulfur Bonds by Rhodococcus sp. Strain WU-K2R

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