ホーム>>Infectious Disease>> Quorum Sensing>>N-3-oxo-octanoyl-L-Homoserine lactone

N-3-oxo-octanoyl-L-Homoserine lactone (Synonyms: 3-oxo-C8-HSL,N-β-oxo-octanoyl-L-Homoserine lactone,N-(3-Oxooctanoyl)-L-homoserine; N-(3-OXOOCTANOYL)-L-HOMOSERINE LACTONE)

カタログ番号GC14832

クオラムセンシングシグナルであるN-3-オキソ-オクタノイル-L-ホモセリンラクトンは、アグロバクテリウムオートインデューサーです。

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N-3-oxo-octanoyl-L-Homoserine lactone 化学構造

Cas No.: 147795-39-9

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5mg
$40.00
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10mg
$71.00
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25mg
$168.00
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50mg
$295.00
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Sample solution is provided at 25 µL, 10mM.

Description of N-3-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.2Coordinated 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

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 Journal of Bacteriology 188(2), 773-783 (2006).
3. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies Nature Reviews.Microbiology 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 Letters 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 Journal of Bacteriology 180(20), 5398-5405 (1998).

Chemical Properties of N-3-oxo-octanoyl-L-Homoserine lactone

Cas No. 147795-39-9 SDF
同義語 3-oxo-C8-HSL,N-β-oxo-octanoyl-L-Homoserine lactone,N-(3-Oxooctanoyl)-L-homoserine; N-(3-OXOOCTANOYL)-L-HOMOSERINE LACTONE
Chemical Name 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
Canonical SMILES O=C1[C@@H](NC(CC(CCCCC)=O)=O)CCO1
Formula C12H19NO4 M.Wt 241.3
溶解度 30mg/mL in DMSO, 30mg/mL in DMF, 1mg/mL in Ethanol Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of N-3-oxo-octanoyl-L-Homoserine lactone

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1 mg 5 mg 10 mg
1 mM 4.1442 mL 20.7211 mL 41.4422 mL
5 mM 0.8288 mL 4.1442 mL 8.2884 mL
10 mM 0.4144 mL 2.0721 mL 4.1442 mL
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