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.
Original language | Unknown |
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Pages (from-to) | 1236-1241 |
Journal | Bioorganic & Medicinal Chemistry |
Volume | 19 |
Issue number | 3 |
DOIs | |
Publication status | Published - 1 Jan 2011 |