Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents
Two analogues of 3-(dimethylsulfonio)propanoate (DMSP), 3-(diallylsulfonio)propanoate (DAllSP), and 3-(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.51 |
| _version_ | 1818556973214334976 |
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| author | Anuj Kumar Chhalodia Jeroen S. Dickschat |
| author_facet | Anuj Kumar Chhalodia Jeroen S. Dickschat |
| author_sort | Anuj Kumar Chhalodia |
| collection | DOAJ |
| description | Two analogues of 3-(dimethylsulfonio)propanoate (DMSP), 3-(diallylsulfonio)propanoate (DAllSP), and 3-(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The DMSP analogues were also degraded, resulting in the release of allylated sulfur volatiles known from garlic. For unknown compounds, structural suggestions were made based on their mass spectrometric fragmentation pattern and confirmed by the synthesis of reference compounds. The results of the feeding experiments allowed to conclude on the substrate tolerance of DMSP degrading enzymes in marine bacteria. |
| first_indexed | 2024-12-13T23:54:05Z |
| format | Article |
| id | doaj.art-9487c95c35454892a90d8e777dec7f94 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:54:05Z |
| publishDate | 2021-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9487c95c35454892a90d8e777dec7f942022-12-21T23:26:40ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-02-0117156958010.3762/bjoc.17.511860-5397-17-51Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituentsAnuj Kumar Chhalodia0Jeroen S. Dickschat1Kekulé Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, GermanyKekulé Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, GermanyTwo analogues of 3-(dimethylsulfonio)propanoate (DMSP), 3-(diallylsulfonio)propanoate (DAllSP), and 3-(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The DMSP analogues were also degraded, resulting in the release of allylated sulfur volatiles known from garlic. For unknown compounds, structural suggestions were made based on their mass spectrometric fragmentation pattern and confirmed by the synthesis of reference compounds. The results of the feeding experiments allowed to conclude on the substrate tolerance of DMSP degrading enzymes in marine bacteria.https://doi.org/10.3762/bjoc.17.51allium sativumallyl sulfides3-(dimethylsulfonio)propanoateroseobactervolatiles |
| spellingShingle | Anuj Kumar Chhalodia Jeroen S. Dickschat Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents Beilstein Journal of Organic Chemistry allium sativum allyl sulfides 3-(dimethylsulfonio)propanoate roseobacter volatiles |
| title | Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents |
| title_full | Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents |
| title_fullStr | Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents |
| title_full_unstemmed | Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents |
| title_short | Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents |
| title_sort | breakdown of 3 allylsulfonio propanoates in bacteria from the roseobacter group yields garlic oil constituents |
| topic | allium sativum allyl sulfides 3-(dimethylsulfonio)propanoate roseobacter volatiles |
| url | https://doi.org/10.3762/bjoc.17.51 |
| work_keys_str_mv | AT anujkumarchhalodia breakdownof3allylsulfoniopropanoatesinbacteriafromtheroseobactergroupyieldsgarlicoilconstituents AT jeroensdickschat breakdownof3allylsulfoniopropanoatesinbacteriafromtheroseobactergroupyieldsgarlicoilconstituents |