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N-3-oxo-octanoyl-L-Homoserine lactone

Cayman Chemical Item Number 10011206

N-β-oxo-octanoyl-L-Homoserine lactone; 3-oxo-C8-HSL (CAS 147795-39-9)

N-3-oxo-octanoyl-L-Homoserine lactone (CAS 147795-39-9)

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Description

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

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).

Synonyms
  • N-β-oxo-octanoyl-L-Homoserine lactone
  • 3-oxo-C8-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​octanamide
CAS Number 147795-39-9
Molecular Formula C12H19NO4
Formula Weight 241.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCC(=O)​CCC(=O)​N[C@H]​1CCOC1=O

Background Reading

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).

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).

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).

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).

González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70(4) 859-875 (2006).

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Size Price Quantity Subtotal
5 mg $23.00 $0.00
10 mg $44.00 $0.00
25 mg $104.00 $0.00
50 mg $184.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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