Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes
Studies of the microbial metabolism of benzo[ b ]thiophene (molecular weight 134) by three Pseudomonas isolates showed the formation of benzothiophene sulfoxide, benzothiophene sulfone, and a sulfur-containing metabolite with a molecular weight of 234. Desulfurization of the high-molecular-weight pr...
Published in: | Applied and Environmental Microbiology |
---|---|
Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
American Society for Microbiology
1994
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1128/aem.60.10.3624-3631.1994 https://journals.asm.org/doi/pdf/10.1128/aem.60.10.3624-3631.1994 |
id |
crasmicro:10.1128/aem.60.10.3624-3631.1994 |
---|---|
record_format |
openpolar |
spelling |
crasmicro:10.1128/aem.60.10.3624-3631.1994 2023-11-05T03:44:43+01:00 Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes Kropp, Kevin G. Gonçalves, José A. Andersson, Jan T. Fedorak, Phillip M. 1994 http://dx.doi.org/10.1128/aem.60.10.3624-3631.1994 https://journals.asm.org/doi/pdf/10.1128/aem.60.10.3624-3631.1994 en eng American Society for Microbiology https://journals.asm.org/non-commercial-tdm-license Applied and Environmental Microbiology volume 60, issue 10, page 3624-3631 ISSN 0099-2240 1098-5336 Ecology Applied Microbiology and Biotechnology Food Science Biotechnology journal-article 1994 crasmicro https://doi.org/10.1128/aem.60.10.3624-3631.1994 2023-10-09T15:56:45Z Studies of the microbial metabolism of benzo[ b ]thiophene (molecular weight 134) by three Pseudomonas isolates showed the formation of benzothiophene sulfoxide, benzothiophene sulfone, and a sulfur-containing metabolite with a molecular weight of 234. Desulfurization of the high-molecular-weight product with nickel boride gave 1-phenylnaphthalene, indicating that the metabolite was benzo[ b ]naphtho[1,2- d ]thiophene. Similarly, the isolates were capable of producing the analogous dimethyl-substituted benzonaphthothiophenes from methylbenzothiophenes that had the methyl substitution on the benzene ring. The formation of benzo[ b ] naphtho[1,2- d ]thiophene was also observed when a petroleum-degrading mixed culture was incubated with benzothiophene-supplemented Prudhoe Bay crude oil. Investigations into the mechanism of formation of these high-molecular-weight compounds showed that they resulted from an abiotic, Diels-Alder-type condensation of two molecules of the sulfoxide, which were microbially produced from the respective benzothiophene, with the subsequent loss of two atoms of hydrogen and oxygen and one atom of sulfur. The condensation products also formed from the sulfoxides of benzothiophene and methylbenzothiophenes when the sulfoxides were enzymatically synthesized by oxidation of the benzothiophene with horse heart cytochrome c and H 2 O 2 . Article in Journal/Newspaper Prudhoe Bay ASM Journals (American Society for Microbiology - via Crossref) Applied and Environmental Microbiology 60 10 3624 3631 |
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 Kropp, Kevin G. Gonçalves, José A. Andersson, Jan T. Fedorak, Phillip M. Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
topic_facet |
Ecology Applied Microbiology and Biotechnology Food Science Biotechnology |
description |
Studies of the microbial metabolism of benzo[ b ]thiophene (molecular weight 134) by three Pseudomonas isolates showed the formation of benzothiophene sulfoxide, benzothiophene sulfone, and a sulfur-containing metabolite with a molecular weight of 234. Desulfurization of the high-molecular-weight product with nickel boride gave 1-phenylnaphthalene, indicating that the metabolite was benzo[ b ]naphtho[1,2- d ]thiophene. Similarly, the isolates were capable of producing the analogous dimethyl-substituted benzonaphthothiophenes from methylbenzothiophenes that had the methyl substitution on the benzene ring. The formation of benzo[ b ] naphtho[1,2- d ]thiophene was also observed when a petroleum-degrading mixed culture was incubated with benzothiophene-supplemented Prudhoe Bay crude oil. Investigations into the mechanism of formation of these high-molecular-weight compounds showed that they resulted from an abiotic, Diels-Alder-type condensation of two molecules of the sulfoxide, which were microbially produced from the respective benzothiophene, with the subsequent loss of two atoms of hydrogen and oxygen and one atom of sulfur. The condensation products also formed from the sulfoxides of benzothiophene and methylbenzothiophenes when the sulfoxides were enzymatically synthesized by oxidation of the benzothiophene with horse heart cytochrome c and H 2 O 2 . |
format |
Article in Journal/Newspaper |
author |
Kropp, Kevin G. Gonçalves, José A. Andersson, Jan T. Fedorak, Phillip M. |
author_facet |
Kropp, Kevin G. Gonçalves, José A. Andersson, Jan T. Fedorak, Phillip M. |
author_sort |
Kropp, Kevin G. |
title |
Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
title_short |
Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
title_full |
Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
title_fullStr |
Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
title_full_unstemmed |
Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[ b ]thiophenes |
title_sort |
microbially mediated formation of benzonaphthothiophenes from benzo[ b ]thiophenes |
publisher |
American Society for Microbiology |
publishDate |
1994 |
url |
http://dx.doi.org/10.1128/aem.60.10.3624-3631.1994 https://journals.asm.org/doi/pdf/10.1128/aem.60.10.3624-3631.1994 |
genre |
Prudhoe Bay |
genre_facet |
Prudhoe Bay |
op_source |
Applied and Environmental Microbiology volume 60, issue 10, page 3624-3631 ISSN 0099-2240 1098-5336 |
op_rights |
https://journals.asm.org/non-commercial-tdm-license |
op_doi |
https://doi.org/10.1128/aem.60.10.3624-3631.1994 |
container_title |
Applied and Environmental Microbiology |
container_volume |
60 |
container_issue |
10 |
container_start_page |
3624 |
op_container_end_page |
3631 |
_version_ |
1781705362291818496 |