C14:1-DELTA9-CIS-(L)-HSL Chemical Properties

Boiling point:

506.5±39.0 °C(Predicted)

Density 

0.99±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

pka

14.70±0.20(Predicted)

color 

White to off-white

InChI

InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1

InChIKey

ZQAYHOXXVBVXPZ-INIZCTEOSA-N

SMILES

C(N[C@H]1CCOC1=O)(=O)CCCCCCCCCCCCC

C14:1-DELTA9-CIS-(L)-HSL Usage And Synthesis

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 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. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain AHLs, stimulates bacterial growth. C₁₄-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.

Uses

Tetradecanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Rhodobacter capsulatus. Tetradecanoyl-L-homoserine lactone and other acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains.

Uses

Tetradecanoyl-L-homoserine lactone is a major modulator for cell communication.

References

[1] A KUO  P V D  N V Blough. Multiple N-acyl-L-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri.[J]. Journal of Bacteriology, 1994, 176 24: 7558-7565. DOI: 10.1128/jb.176.24.7558-7565.1994
[2] J K LITHGOW. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci.[J]. Molecular Microbiology, 2000, 37 1: 81-97. DOI: 10.1046/j.1365-2958.2000.01960.x
[3] KAY H MCCLEAN. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones.[J]. Microbiology-Sgm, 1997, 143 ( Pt 12): 3703-3711. DOI: 10.1099/00221287-143-12-3703
[4] YI-LI HUANG. Evidence for the dynamics of Acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation[J]. ISME Journal, 2008, 3 3: 296-304. DOI: 10.1038/ismej.2008.105
[5] JEAN J HUANG. Utilization of acyl-homoserine lactone quorum signals for growth by a soil pseudomonad and Pseudomonas aeruginosa PAO1.[J]. Applied and Environmental Microbiology, 2003, 69 10: 5941-5949. DOI: 10.1128/aem.69.10.5941-5949.2003
[6] DOROTA STANKOWSKA  Wieslaw K  Marek Kwinkowski. Quantification of Proteus mirabilis virulence factors and modulation by acylated homoserine lactones.[J]. Journal of Microbiology Immunology and Infection, 2008, 41 3: 243-253.

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