(Z)-N-[(3S)-2-oxooxolan-3-yl]tetradec-9-enamide

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density.¹ This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.² Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C₄-C₁₈), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family.³ C₁₄:1-Δ⁹-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis.⁴ Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.⁵

ChEBI: N-cis-tetradec-9Z-enoyl-L-Homoserine lactone is a N-acyl-amino acid.

1. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing Microbiol. Mol. Biol. Rev. 70(4),859-875(2006).
2. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry J. Bacteriol. 188(2),773-783(2006).
3. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions FEBS Lett. 580(2),561-567(2006).
4. Li, Y., Gronquist, M.R., Hao, G., et al. Chromosome and plasmid-encoded N-acyl homoserine lactones produced by Agrobacterium vitis wildtype and mutants that differ in their interactions with grape and tobacco Physiol. Mol. Plant Pathol. 67,284-290(2006).
5. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies Nat. Rev. Microbiol. 6(1),17-27(2008).