An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2
A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-<sup>13</sup>C]-AI-2 starting from [1-<sup>13</sup>C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/2/369 |
| _version_ | 1797412484775149568 |
|---|---|
| author | Osvaldo S. Ascenso Gonzalo Carrau Karina B. Xavier M. Rita Ventura Christopher D. Maycock |
| author_facet | Osvaldo S. Ascenso Gonzalo Carrau Karina B. Xavier M. Rita Ventura Christopher D. Maycock |
| author_sort | Osvaldo S. Ascenso |
| collection | DOAJ |
| description | A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-<sup>13</sup>C]-AI-2 starting from [1-<sup>13</sup>C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate ketone. This synthesis provides, selectively, both enantiomers of the labelled or unlabelled parent compound, (<i>R</i>) or (<i>S</i>)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-<sup>13</sup>C]-AI-2. |
| first_indexed | 2024-03-09T05:03:20Z |
| format | Article |
| id | doaj.art-3e32d47d5c3d4aaca9263f13a583bae7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:03:20Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3e32d47d5c3d4aaca9263f13a583bae72023-12-03T12:57:39ZengMDPI AGMolecules1420-30492021-01-0126236910.3390/molecules26020369An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2Osvaldo S. Ascenso0Gonzalo Carrau1Karina B. Xavier2M. Rita Ventura3Christopher D. Maycock4Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, PortugalInstituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, PortugalInstituto Gulbenkian de Ciência, 2780-156 Oeiras, PortugalInstituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, PortugalInstituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, PortugalA new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-<sup>13</sup>C]-AI-2 starting from [1-<sup>13</sup>C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate ketone. This synthesis provides, selectively, both enantiomers of the labelled or unlabelled parent compound, (<i>R</i>) or (<i>S</i>)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-<sup>13</sup>C]-AI-2.https://www.mdpi.com/1420-3049/26/2/369DPDAI-2quorum sensingenantioselective synthesis<sup>13</sup>C-DPD |
| spellingShingle | Osvaldo S. Ascenso Gonzalo Carrau Karina B. Xavier M. Rita Ventura Christopher D. Maycock An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 Molecules DPD AI-2 quorum sensing enantioselective synthesis <sup>13</sup>C-DPD |
| title | An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 |
| title_full | An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 |
| title_fullStr | An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 |
| title_full_unstemmed | An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 |
| title_short | An Efficient Synthesis of Optically Active [4-<sup>13</sup>C] Labelled Quorum Sensing Signal Autoinducer-2 |
| title_sort | efficient synthesis of optically active 4 sup 13 sup c labelled quorum sensing signal autoinducer 2 |
| topic | DPD AI-2 quorum sensing enantioselective synthesis <sup>13</sup>C-DPD |
| url | https://www.mdpi.com/1420-3049/26/2/369 |
| work_keys_str_mv | AT osvaldosascenso anefficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT gonzalocarrau anefficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT karinabxavier anefficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT mritaventura anefficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT christopherdmaycock anefficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT osvaldosascenso efficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT gonzalocarrau efficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT karinabxavier efficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT mritaventura efficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 AT christopherdmaycock efficientsynthesisofopticallyactive4sup13supclabelledquorumsensingsignalautoinducer2 |