An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing
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.
Ascenso, Osvaldo S.,Marques, Jo?o C.,Santos, Ana Rita,Xavier, Karina B.,Rita Ventura,Maycock, Christopher D.
experimental part
p. 1236 - 1241
(2011/03/22)
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