3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]octanamide

Product Name3-hydroxy-N-[(3S)-2-oxooxolan-3-yl]octanamide
CAS192883-14-0
MFC12H21NO4
MW243.3
EINECS
MOL File192883-14-0.mol

Chemical Properties

Boiling point	504.7±50.0 °C(Predicted)
Density	1.13±0.1 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMF: 30 mg/ml; DMSO: 30 mg/ml
form	A crystalline solid
pka	14.27±0.20(Predicted)

Usage And Synthesis

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Different quorum sensing molecules are produced at different times in bacterial population growth and have distinct cellular effects mediated through changes in gene expression. N-3-hydroxyoctanoyl-L-Homoserine lactone is a small diffusible signaling molecule secreted by various bacteria. This lactone can have activating or suppressing effects on gene expression and biofilm formation, respectively. N-3-hydroxyoctanoyl-L-Homoserine lactone is produced via lactonolysis from 3-oxooctanoyl-homoserine lactone, altering quorum sensing or contributing to quorum quenching.

Uses

N-(3-Hydroxyoctanoyl)-L-homoserine Lactone is a homoserine lactones found in Bacteria. Used by wide variety of bacteria for cell-cell communication in "quorum-sensing.

Definition

ChEBI: 3-Hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide is a N-acyl-amino acid.

References

[1] SREN KRISTIANSEN. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells[J]. Apmis, 2008, 116 5: 361-371. DOI: 10.1111/j.1600-0463.2008.00966.x
[2] L R FLODGAARD. Nonbioluminescent strains of Photobacterium phosphoreum produce the cell-to-cell communication signal N-(3-Hydroxyoctanoyl)homoserine lactone.[J]. Applied and Environmental Microbiology, 2005, 71 4: 2113-2120. DOI: 10.1128/aem.71.4.2113-2120.2005
[3] PUTTHAPOOM LUMJIAKTASE. Quorum sensing regulates dpsA and the oxidative stress response in Burkholderia pseudomallei.[J]. Microbiology-Sgm, 2006, 152 Pt 12: 3651-3659. DOI: 10.1099/mic.0.29226-0
[4] BRECK A DUERKOP. The Burkholderia mallei BmaR3-BmaI3 quorum-sensing system produces and responds to N-3-hydroxy-octanoyl homoserine lactone.[J]. Journal of Bacteriology, 2008, 190 14: 5137-5141. DOI: 10.1128/jb.00246-08
[5] AKSHAMAL MIHIRANGA GAMAGE. N-Octanoylhomoserine lactone signalling mediated by the BpsI-BpsR quorum sensing system plays a major role in biofilm formation of Burkholderia pseudomallei.[J]. Microbiology-Sgm, 2011, 157 Pt 4: 1176-1186. DOI: 10.1099/mic.0.046540-0
[6] KOK-GAN CHAN. Characterization of N-acylhomoserine lactone-degrading bacteria associated with the Zingiber officinale (ginger) rhizosphere: co-existence of quorum quenching and quorum sensing in Acinetobacter and Burkholderia.[J]. BMC Microbiology, 2011, 11: 51. DOI: 10.1186/1471-2180-11-51

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