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N-3-oxo-tetradec-7(Z)-enoyl-L-Homoserine lactone

Cayman Chemical Item Number 13213

3-oxo-C14:1-Δ7cis-(L)-HSL (CAS 482598-46-9)

N-3-oxo-tetradec-7(Z)-enoyl-L-Homoserine lactone (CAS 482598-46-9)

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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 3-oxo-C14:1-Δ7cis-(L)-HSL is a bacterial quorum sensing compound that possesses antimicrobial activity, the ability to inhibit biofilm formation, and exhibits immune suppressive activity.5,6 This compound is structurally related to other 3-oxo-monounsaturated (N-acylated homoserine lactones) AHLs such as 3-oxo-C16:1-Δ11cis-(L)-HSL (Catalog No. 10011238).

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 Woodard, B., and Saleh, M.A. Three-dimensional quantitative structure activity relationships of quorum-sensing and biofilm inhibitors in gram-negative bacteria. J Environ Sci Health B 43(4) 281-287 (2008).

6 Chhabra, S.R., Harty, C., Hooi, D.S.W., et al. Synthetic analogues of the bacterial signal (quorum seensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators. J Med Chem 46 97-104 (2003).

Synonyms
  • 3-oxo-C14:1-Δ7cis-(L)-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​7-​tetradecenamide
CAS Number 482598-46-9
Molecular Formula C18H29NO4
Formula Weight 323.4
Formulation A solution in acetonitrile
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
O=C1[C@@H]​(NC(CC(CCC/C=C\CCCCCC)​=O)​=O)​CCO1

Background Reading

Chhabra, S.R., Harty, C., Hooi, D.S.W., et al. Synthetic analogues of the bacterial signal (quorum seensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators. J Med Chem 46 97-104 (2003).

Woodard, B., and Saleh, M.A. Three-dimensional quantitative structure activity relationships of quorum-sensing and biofilm inhibitors in gram-negative bacteria. J Environ Sci Health B 43(4) 281-287 (2008).

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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N-3-oxo-tetradec-7(Z)-enoyl-L-Homoserine lactone is available in the following screening library:

Size Price Quantity Subtotal
1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
25 mg $403.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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