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N-3-oxo-tetradecanoyl-L-Homoserine lactone

(Synonyms: N-(3-氧代十四烷酰基)-L-高丝氨酸内酯,3-oxo-C14-HSL; N-3-oxo-myristoyl-L-Homoserine lactone) 目录号 : GC44288

3-oxo-C14 quorum-sensing lactone

N-3-oxo-tetradecanoyl-L-Homoserine lactone Chemical Structure

Cas No.:177158-19-9

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1mg
¥411.00
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5mg
¥1,850.00
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10mg
¥3,289.00
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25mg
¥7,195.00
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Sample solution is provided at 25 µL, 10mM.

Description

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 LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-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 3-oxo-AHLs, stimulates the production of putisolvin, [5] which in turn, inhibits biofilm formation.

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]. Gomi, K., Kikuchi, T., Tokue, Y., et al. Mouse and human cell activation by N-dodecanoyl-DL-homoserine lactone, a Chromobacterium violaceum autoinducer. Infection and Immunity 74(12), 7029-7031 (2006).
[5]. Dubern, J.F., Lugtenberg, B.J.J., and Bloemberg, G.V. The ppuI-rsaL-ppuR quorum-sensing system regulates biofilm formation of Pseudomonas putida PCL1445 by controlling biosynthesis of the Cyclic Lipopeptides Putisolvins I and II. Journal of Bacteriology 188(8), 2898-2906 (2006).

化学性质

Cas No. 177158-19-9 SDF
别名 N-(3-氧代十四烷酰基)-L-高丝氨酸内酯,3-oxo-C14-HSL; N-3-oxo-myristoyl-L-Homoserine lactone
化学名 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-tetradecanamide
Canonical SMILES CCCCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
分子式 C18H31NO4 分子量 325.4
溶解度 DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 3.0731 mL 15.3657 mL 30.7314 mL
5 mM 0.6146 mL 3.0731 mL 6.1463 mL
10 mM 0.3073 mL 1.5366 mL 3.0731 mL
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