RRC ID 35346
Author Ascenso OS, Marques JC, Santos AR, Xavier KB, Ventura MR, Maycock CD.
Title An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
Journal Bioorg. Med. Chem.
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.
Volume 19(3)
Pages 1236-41
Published 2011-2-1
DOI 10.1016/j.bmc.2010.12.036
PII S0968-0896(10)01127-2
PMID 21216605
MeSH Drug Contamination Escherichia coli / genetics Escherichia coli / physiology* Homoserine / analogs & derivatives* Homoserine / chemistry Homoserine / metabolism Lactones / chemistry* Lactones / metabolism* Pentanones / chemical synthesis* Pentanones / metabolism Quorum Sensing* Reproducibility of Results
IF 2.881
Times Cited 15
WOS Category CHEMISTRY, MEDICINAL CHEMISTRY, ORGANIC BIOCHEMISTRY & MOLECULAR BIOLOGY
Resource
Prokaryotes E. coli NA