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N-3-hydroxydecanoyl-L-Homoserine lactone Exclusive
Cayman Chemical Item Number 9001147
OH-C10-HSL (CAS 192883-12-8)
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-hydroxydecanoyl-L-Homoserine lactone is a small diffusible signaling molecule secreted by various bacteria.3↗,4↗ This lactone is produced via lactonolysis from 3-oxodecanoyl-homoserine lactone, altering quorum sensing or contributing to quorum quenching.5↗
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 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).
4 Fekete, A., Frommberger, M., Rothballer, M., et al. Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors. Anal Bioanal Chem 387 455-467 (2007).
5 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-C10-HSL
Formal Name 3-hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-decanamide
CAS Number 192883-12-8
Molecular Formula C14H25NO4
Formula Weight 271.4
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)CCCCCCC)=O)CCO1
InCHI Code Copy 1S/C14H25NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h11-12,16H,2-10H2,1H3,(H,15,17)/t11?,12-/m0/s1
InCHI Key Copy DOICJCCMIBBSOO-KIYNQFGBSA-N |