| 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 |
3.073
|
| Times Cited |
29
|
|
WOS Category
|
CHEMISTRY, MEDICINAL
CHEMISTRY, ORGANIC
BIOCHEMISTRY & MOLECULAR BIOLOGY
|
| Resource |
| Prokaryotes E. coli |
NA |
