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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Detalles Bibliográficos
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
Descripción
Sumario: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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