An Efficient Synthesis of Optically Active [4-13C] Labelled Quorum Sensing Signal Autoinducer-2 |
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| Authors: | Osvaldo S Ascenso Gonzalo Carrau Karina B Xavier M Rita Ventura Christopher D Maycock |
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| Institution: | 1.Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, Portugal; (O.S.A.); (G.C.);2.Facultad de Química, Universidad de la República, Montevideo 11800, Uruguay;3.Instituto Gulbenkian de Ciência, 2780-156 Oeiras, Portugal;4.Faculdade de Ciências da Universidade de Lisboa, Departamento de Química e Bioquímica, 1749-016 Lisboa, Portugal |
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| Abstract: | A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of 4-13C]-AI-2 starting from 1-13C]-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 1-13C]-AI-2. |
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| Keywords: | DPD AI-2 quorum sensing enantioselective synthesis 13C-DPD |
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