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Bioorg Med Chem. 2011 Feb 1;19(3):1236-41. doi: 10.1016/j.bmc.2010.12.036. Epub 2010 Dec 21.

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

Author information

1
Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Apartado 127, 2780-901 Oeiras, Portugal.

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.

PMID:
21216605
DOI:
10.1016/j.bmc.2010.12.036
[Indexed for MEDLINE]

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