Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene
A culture enriched by growth on 1-methylnaphthalene was used to study the aerobic biotransformations of benzothiophene and 3-methylbenzothiophene. Neither of the sulfur heterocyclic compounds would support growth, but they were transformed by the culture growing on 1-methylnaphthalene or glucose or...
Published in: | Applied and Environmental Microbiology |
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American Society for Microbiology
1991
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Online Access: | http://dx.doi.org/10.1128/aem.57.4.932-940.1991 https://journals.asm.org/doi/pdf/10.1128/aem.57.4.932-940.1991 |
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crasmicro:10.1128/aem.57.4.932-940.1991 2023-11-05T03:44:43+01:00 Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene Fedorak, Phillip M. Grbić-Galić, Dunja 1991 http://dx.doi.org/10.1128/aem.57.4.932-940.1991 https://journals.asm.org/doi/pdf/10.1128/aem.57.4.932-940.1991 en eng American Society for Microbiology https://journals.asm.org/non-commercial-tdm-license Applied and Environmental Microbiology volume 57, issue 4, page 932-940 ISSN 0099-2240 1098-5336 Ecology Applied Microbiology and Biotechnology Food Science Biotechnology journal-article 1991 crasmicro https://doi.org/10.1128/aem.57.4.932-940.1991 2023-10-09T16:03:56Z A culture enriched by growth on 1-methylnaphthalene was used to study the aerobic biotransformations of benzothiophene and 3-methylbenzothiophene. Neither of the sulfur heterocyclic compounds would support growth, but they were transformed by the culture growing on 1-methylnaphthalene or glucose or peptone. Cometabolism of benzothiophene yielded benzothiophene-2,3-dione, whereas that of 3-methylbenzothiophene yielded 3-methylbenzothiophene sulfoxide and the corresponding sulfone. The identities of the dione and sulfone were verified by comparison with authentic standards. The identity of the sulfoxide was surmised from gas chromatography-mass spectrometry and gas chromatography- Fourier transform infrared spectroscopy results. Oxidation preferentially occurred at carbons 2 and 3 in benzothiophene, but when carbon 3 was substituted with a methyl group, as in 3-methylbenzothiophene, the sulfur atom was oxygenated. The predominant microorganism in the enrichment culture was a Pseudomonas strain, designated BT1, which mineralized aromatic but not aliphatic hydrocarbons. This isolate cometabolized benzothiophene and 3-methylbenzothiophene. There was no evidence that it could metabolize 3-methylbenzothiophene sulfone. When 3-methylbenzothiophene was added to Prudhoe Bay crude oil, the sulfur heterocycle was oxidized to its sulfoxide and sulfone by strain BT1 as it grew on the aromatic hydrocarbons in the crude oil. Benzothiophene-2,3-dione was found to be chemically unstable when incubated with Prudhoe Bay crude oil. Thus its formation from benzothiophene in the presence of crude oil could not be determined. Article in Journal/Newspaper Prudhoe Bay ASM Journals (American Society for Microbiology - via Crossref) Applied and Environmental Microbiology 57 4 932 940 |
institution |
Open Polar |
collection |
ASM Journals (American Society for Microbiology - via Crossref) |
op_collection_id |
crasmicro |
language |
English |
topic |
Ecology Applied Microbiology and Biotechnology Food Science Biotechnology |
spellingShingle |
Ecology Applied Microbiology and Biotechnology Food Science Biotechnology Fedorak, Phillip M. Grbić-Galić, Dunja Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
topic_facet |
Ecology Applied Microbiology and Biotechnology Food Science Biotechnology |
description |
A culture enriched by growth on 1-methylnaphthalene was used to study the aerobic biotransformations of benzothiophene and 3-methylbenzothiophene. Neither of the sulfur heterocyclic compounds would support growth, but they were transformed by the culture growing on 1-methylnaphthalene or glucose or peptone. Cometabolism of benzothiophene yielded benzothiophene-2,3-dione, whereas that of 3-methylbenzothiophene yielded 3-methylbenzothiophene sulfoxide and the corresponding sulfone. The identities of the dione and sulfone were verified by comparison with authentic standards. The identity of the sulfoxide was surmised from gas chromatography-mass spectrometry and gas chromatography- Fourier transform infrared spectroscopy results. Oxidation preferentially occurred at carbons 2 and 3 in benzothiophene, but when carbon 3 was substituted with a methyl group, as in 3-methylbenzothiophene, the sulfur atom was oxygenated. The predominant microorganism in the enrichment culture was a Pseudomonas strain, designated BT1, which mineralized aromatic but not aliphatic hydrocarbons. This isolate cometabolized benzothiophene and 3-methylbenzothiophene. There was no evidence that it could metabolize 3-methylbenzothiophene sulfone. When 3-methylbenzothiophene was added to Prudhoe Bay crude oil, the sulfur heterocycle was oxidized to its sulfoxide and sulfone by strain BT1 as it grew on the aromatic hydrocarbons in the crude oil. Benzothiophene-2,3-dione was found to be chemically unstable when incubated with Prudhoe Bay crude oil. Thus its formation from benzothiophene in the presence of crude oil could not be determined. |
format |
Article in Journal/Newspaper |
author |
Fedorak, Phillip M. Grbić-Galić, Dunja |
author_facet |
Fedorak, Phillip M. Grbić-Galić, Dunja |
author_sort |
Fedorak, Phillip M. |
title |
Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
title_short |
Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
title_full |
Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
title_fullStr |
Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
title_full_unstemmed |
Aerobic Microbial Cometabolism of Benzothiophene and 3-Methylbenzothiophene |
title_sort |
aerobic microbial cometabolism of benzothiophene and 3-methylbenzothiophene |
publisher |
American Society for Microbiology |
publishDate |
1991 |
url |
http://dx.doi.org/10.1128/aem.57.4.932-940.1991 https://journals.asm.org/doi/pdf/10.1128/aem.57.4.932-940.1991 |
genre |
Prudhoe Bay |
genre_facet |
Prudhoe Bay |
op_source |
Applied and Environmental Microbiology volume 57, issue 4, page 932-940 ISSN 0099-2240 1098-5336 |
op_rights |
https://journals.asm.org/non-commercial-tdm-license |
op_doi |
https://doi.org/10.1128/aem.57.4.932-940.1991 |
container_title |
Applied and Environmental Microbiology |
container_volume |
57 |
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4 |
container_start_page |
932 |
op_container_end_page |
940 |
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1781705361903845376 |