N-3-oxo-hexadec-11(Z)-enoyl-L-Homoserine lactone
Item № 10011238
CAS № 1269663-80-0
Purity ≥98%
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1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
25 mg $403.00 $0.00

Pricing updated 2015-11-26. Prices are subject to change without notice.

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  • 3-oxo-C16:1-Δ11cis-(L)-HSL

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 An unspecified positional and geometric isomer of 3-oxo-C16:1-(L)-HSL is produced by the F2/5 strain of A. vitis, the bacterium responsible for grape crown gall and its resulting loss of agricultural productivity.5

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Technical Information
Formal Name 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-(11Z)-hexadecenamide
CAS Number 1269663-80-0
  • 3-oxo-C16:1-Δ11cis-(L)-HSL
Molecular Formula C20H33NO4
Formula Weight 351.5
Purity ≥98%
Formulation A solution in acetonitrile
λmax 246 nm
InChI Code 1S/C20H33NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-19(23)21-18-14-15-25-20(18)24/h5-6,18H,2-4,7-16H2,1H3,(H,21,23)/b6-5-/t18-/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 1 year
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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. Hao, G., and Burr, T.J. Regulation of long-chain N-acyl-homoserine lactones in agrobacterium vitis. J Bacteriol 188(6) 2173-2183 (2006).

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