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N-3-hydroxyoctanoyl-L-Homoserine lactone Exclusive
Cayman Chemical Item Number 9001150
OH-C8-HSL (CAS 192883-14-0)
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.1↗,2↗ N-3-hydroxyoctanoyl-L-Homoserine lactone is a small diffusible signaling molecule secreted by various bacteria.3↗,4↗ This lactone can have activating or suppressing effects on gene expression and biofilm formation, respectively.5↗,6↗ N-3-hydroxyoctanoyl-L-Homoserine lactone is produced via lactonolysis from 3-oxooctanoyl-homoserine lactone, altering quorum sensing or contributing to quorum quenching.7↗
1 Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS 116 361-371 (2008).
2 Huang, Y., Ki, J., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J 1-9 (2008).
3 Flodgaard, L.R., Dalgaard, P., Andersen, J.B., et al. Nonbioluminescent strains of Photobacterium phosphoreum produce the cell-to-cell communication signal N-(3-hydroxyoctanoyl)homoserine lactone. Appl Environ Microbiol 71(4) 2113-2120 (2005).
4 Lumjiaktase, P., Diggle, S.P., Loprasert, S., et al. Quorum sensing regulates dpsA and the oxidative stress response in Burkholderia pseudomallei. Microbiology 152 3651-3659 (2006).
5 Duerkop, B.A., Herman, J.P., Ulrich, R.L., et al. The Burkholderia mallei BmaR3-BmaI3 quorum-sensing system produces and responds to N-3-hydroxy-octanoyl homoserine lactone. J Bacteriol 190(14) 5137-5141 (2008).
6 Gamage, A.M., Shui, G., Wenk, M.R., et al. N-Octanoylhomoserine lactone signalling mediated by the BpsI-BpsR quorum sensing system plays a major role in biofilm formation of Burkholderia pseudomallei. Microbiology 157 1176-1186 (2011).
7 Chan, K., Atkinson, S., Mathee, K., et al. 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. BMC Microbiol 11(51) 1-13 (2011).
Synonyms OH-C8-HSL
Formal Name 3-hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
CAS Number 192883-14-0
Molecular Formula C12H21NO4
Formula Weight 243.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES Copy O=C1[C@@H](NC(CC(O)CCCCC)=O)CCO1
InCHI Code Copy 1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)/t9?,10-/m0/s1
InCHI Key Copy XCZVBYOXRSFQBH-AXDSSHIGSA-N |