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N-octanoyl-L-Homoserine lactone

(Synonyms: 辛酰基-L-高丝氨酸内酯,C8-HSL,OHL) 目录号 : GC12708

A bacterial quorum sensing signal molecule

N-octanoyl-L-Homoserine lactone Chemical Structure

Cas No.:147852-84-4

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产品描述

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 synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-

octanoyl-L-Homoserine lactone (C8-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism.1,2,3 The applications of this molecule include infection prevention and regulation of virulence in general and in cystic fibrosis.4,5

References
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. Riedel, K., Hentzer, M., Geisenberger, O., et al. N-acylhomoserine-lactone-mediated communication between Pseudomonas aeruginosa and Burkholderia cepacia in mixed biofilms Microbiology 147, 3249-3262 (2001).
5. Winson, M.K., Camara, M., Latifi, A., et al. Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa Proceedings of the National Academy of Sciences of the United States of America 92, 9427-9431 (1995).

Chemical Properties

Cas No. 147852-84-4 SDF
别名 辛酰基-L-高丝氨酸内酯,C8-HSL,OHL
化学名 N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
Canonical SMILES CCCCCCCC(=O)C[C@H]1CCOC1=O
分子式 C12H21NO3 分子量 227.3
溶解度 DMF: 25 mg/ml,DMF:PBS(pH7.2) 1:2: 0.3 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 mg/ml 储存条件 Store at -20°C
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1 mM 4.3995 mL 21.9974 mL 43.9947 mL
5 mM 0.8799 mL 4.3995 mL 8.7989 mL
10 mM 0.4399 mL 2.1997 mL 4.3995 mL
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