RRC ID |
35346
|
著者 |
Ascenso OS, Marques JC, Santos AR, Xavier KB, Ventura MR, Maycock CD.
|
タイトル |
An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
|
ジャーナル |
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.
|
巻・号 |
19(3)
|
ページ |
1236-41
|
公開日 |
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 |
3.073
|
引用数 |
29
|
WOS 分野
|
CHEMISTRY, MEDICINAL
CHEMISTRY, ORGANIC
BIOCHEMISTRY & MOLECULAR BIOLOGY
|
リソース情報 |
原核生物(大腸菌) |
NA |