N-[(3S)-Tetrahydro-2-oxo-3-furanyl]butanamide

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-butyryl-L-Homoserine lactone is a quorum-sensing signaling molecule produced by P. aeruginosa. It induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 μM. N-butyryl-L-Homoserine lactone (50 μM) induces rhamnolipid accumulation in P. aeruginosa growth media.

Uses

N-butyryl-L-Homoserine lactone is a diffusable quorum sensing lactone.

Uses

Butyryl-L-homoserine lactone is a short acylhomoserine lactone isolated from Pseudomonas aeruginosa in 1995 and demonstrated to be a quorum sensing modulator in biofilms. Acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorterchains displaying opposing actions to the longer chains.

Definition

ChEBI: (+)-a(S)-butyr-amido-r-butyrolactone is a N-acyl-amino acid.

IC 50

Cleavable Linker

References

[1] J P PEARSON. A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1995, 92 5: 1490-1494. DOI: 10.1073/pnas.92.5.1490
[2] T. IKEDA. Synthesis of Optically Pure Enantiomers of N-Acyl-homoserine Lactone Autoinducers and Their Analogues.[J]. ChemInform, 2001, 48 1. DOI: 10.1002/chin.200134195
[3] S. SCHOOLING. A role for rhamnolipid in biofilm dispersion[J]. Biofilms, 2004, 1 1: 91-99. DOI: 10.1017/s147905050400119x