N-3-oxo-octanoyl-L-Homoserine lactone
Item № 10011206
CAS № 147795-39-9
Purity ≥98%
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5 mg $23.00 $0.00
10 mg $44.00 $0.00
25 mg $104.00 $0.00
50 mg $184.00 $0.00

Pricing updated 2015-12-02. Prices are subject to change without notice.

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  • 3-oxo-C8-HSL
  • N-β-oxo-octanoyl-L-Homoserine lactone

Quorum sensing is a regulatory system 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). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases.3 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.4 In the gram-negative bacterium A. tumefaciens, N-3-oxo-octanoyl-L-homoserine lactone promotes the expression of the transcriptional activator (and LuxR homolog) TraR.5

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Technical Information
Formal Name 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
CAS Number 147795-39-9
  • 3-oxo-C8-HSL
  • N-β-oxo-octanoyl-L-Homoserine lactone
Molecular Formula C12H19NO4
Formula Weight 241.3
Purity ≥98%
Formulation A crystalline solid
InChI Code 1S/C13H21NO4/c1-2-3-4-5-10(15)6-7-12(16)14-11-8-9-18-13(11)17/h11H,2-9H2,1H3,(H,14,16)/t11-/m0/s1

WARNING - This product is not for human or veterinary use.

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Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 2 years
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References & Background Reading
Product Description References

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. 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).

4. 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 580 561-567 (2006).

5. Zhu, J., Beaber, J.W., Moré, M.I., et al. Analogs of the autoinducer 3-oxooctanoyl-homoserine lactone strongly inhibit activity of the TraR protein of Agrobacterium tumefaciens. J Bacteriol 180(20) 5398-5405 (1998).

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