An Efficient Synthesis of Optically Active [4-(13)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-(13)C]-AI-2 starting from [1-(13)C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate ketone. This synthesis provides, selective...

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Autores principales: Ascenso, Osvaldo S., Carrau, Gonzalo, Xavier, Karina B., Ventura, M. Rita, Maycock, Christopher D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828210/
https://www.ncbi.nlm.nih.gov/pubmed/33445716
http://dx.doi.org/10.3390/molecules26020369
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author Ascenso, Osvaldo S.
Carrau, Gonzalo
Xavier, Karina B.
Ventura, M. Rita
Maycock, Christopher D.
author_facet Ascenso, Osvaldo S.
Carrau, Gonzalo
Xavier, Karina B.
Ventura, M. Rita
Maycock, Christopher D.
author_sort Ascenso, Osvaldo S.
collection PubMed
description A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-(13)C]-AI-2 starting from [1-(13)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, (R) or (S)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-(13)C]-AI-2.
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spelling pubmed-78282102021-01-25 An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2 Ascenso, Osvaldo S. Carrau, Gonzalo Xavier, Karina B. Ventura, M. Rita Maycock, Christopher D. Molecules Article A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-(13)C]-AI-2 starting from [1-(13)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, (R) or (S)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-(13)C]-AI-2. MDPI 2021-01-12 /pmc/articles/PMC7828210/ /pubmed/33445716 http://dx.doi.org/10.3390/molecules26020369 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ascenso, Osvaldo S.
Carrau, Gonzalo
Xavier, Karina B.
Ventura, M. Rita
Maycock, Christopher D.
An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title_full An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title_fullStr An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title_full_unstemmed An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title_short An Efficient Synthesis of Optically Active [4-(13)C] Labelled Quorum Sensing Signal Autoinducer-2
title_sort efficient synthesis of optically active [4-(13)c] labelled quorum sensing signal autoinducer-2
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828210/
https://www.ncbi.nlm.nih.gov/pubmed/33445716
http://dx.doi.org/10.3390/molecules26020369
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