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N-tetradecanoyl-L-Homoserine lactone (Synonyms: C14-HSL, tDHL)

Catalog No.GC19513

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density

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N-tetradecanoyl-L-Homoserine lactone  Chemical Structure

Cas No.: 202284-87-5

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10mg
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Sample solution is provided at 25 µL, 10mM.

Description of N-tetradecanoyl-L-Homoserine lactone

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-tetradecanoyl-L-Homoserine lactone (C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1],[2],[3] It appears later than shorter acyl chain AHLs in developing biofilms[4] and, like other long chain AHLs, stimulates bacterial growth.[5] C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.[6]

Reference:

[1]. Kuo, A., Blough, N.V., and Dunlap, P.V. Multiple N-acyl-L-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri Journal of Bacteriology 176(24), 7558-7565 (1994).
[2]. Lithgow, J.K., Wilkinson, A., Hardman, A., et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci Molecular Microbiology 37(1), 81-97 (2000).
[3]. McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones Microbiology 143, 3703-3711 (1997).
[4]. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation ISME Journal 1-9 (2008).
[5]. Huang, J.J., Han, J.I., Zhang, L.H., et al. Utilization of acyl-homoserine lactone quorum signals for growth by a soil pseudomonad and Pseudomonas aeruginosa PAO1 Applied and Environmental Microbiology 69(10), 5941-5949 (2003).
[6]. Stankowska, D., Kwinkowski, M., and Kaca, W. Quantification of Proteus mirabilis virulence factors and modulation by acylated homoserine lactones Journal of Microbiology, Immunology, and Infection 41, 243-253 (2008).

Chemical Properties of N-tetradecanoyl-L-Homoserine lactone

Cas No. 202284-87-5 SDF
Synonyms C14-HSL, tDHL
Chemical Name N-[(3S)-tetrahydro-2-oxo-3-furanyl]-tetradecanamide
Canonical SMILES CCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
Formula C18H33NO3 M.Wt 311.5
Solubility 30mg/mL in DMSO or in DMF 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-tetradecanoyl-L-Homoserine lactone

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1 mg 5 mg 10 mg
1 mM 3.2103 mL 16.0514 mL 32.1027 mL
5 mM 0.6421 mL 3.2103 mL 6.4205 mL
10 mM 0.321 mL 1.6051 mL 3.2103 mL
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