An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.

Basic Information

ID: ALA1671774

Journal: Bioorg Med Chem

Title: An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.

Authors: Ascenso OS, Marques JC, Santos AR, Xavier KB, Ventura MR, Maycock CD.

Abstract: Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter.

CiteXplore: 21216605

DOI: 10.1016/j.bmc.2010.12.036

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