Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers.
The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.
Olsen
J A
JA
Department of Chemistry, Bld. 207, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark.
Severinsen
R
R
Rasmussen
T B
TB
Hentzer
M
M
Givskov
M
M
Nielsen
J
J
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D001426:Bacterial Proteins / Q000737:chemistry*; D015964:Gene Expression Regulation, Bacterial / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects* / Q000235:genetics; D007202:Indicators and Reagents; D049449:Luminescence; D010675:Pheromones / Q000737:chemistry* / Q000494:pharmacology*; D015398:Signal Transduction / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014733:Vibrio / Q000187:drug effects / Q000235:genetics
D001426:Bacterial Proteins; D007202:Indicators and Reagents; D010675:Pheromones; C088386:homoserine lactone; D015107:4-Butyrolactone