期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 19, 期 3, 页码 1236-1241出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.12.036
关键词
DPD; AI-2; Quorum sensing; Enantioselective reduction; C-13-DPD
资金
- Fundacao para a Ciencia e Tecnologia, Portugal [PPCDT/DG/BIA/82010/2006]
- FEDER [REDE/1517/RMN/2005]
- Fundacao para a Ciencia e a Tecnologia (FCT)
- Fundação para a Ciência e a Tecnologia [PPCDT/DG/BIA/82010/2006] Funding Source: FCT
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. (C) 2010 Elsevier Ltd. All rights reserved.
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