LIPID MAPS

Common Name

N-(3-hydroxy-octanoyl)-homoserine lactone

Systematic Name

N-(3-hydroxy-octanoyl)-homoserine lactone

Synonyms

3-hydroxy-C8-HSL
3OH-C8-HSL

LM ID

LMFA08030036

Formula

C₁₂H₂₁NO₄

Exact Mass

Calculate m/z

243.147059

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Category

Main Class

Sub Class

Fatty Acyls [FA]

Fatty amides [FA08]

Fatty acyl homoserine lactones [FA0803]

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

This information has been provided by Cayman Chemical

References

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(5), 361-371 (2008).

2. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J. 3(3), 296-304 (2008).

3. Chan, K.G., 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).

4. 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).

5. 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).

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 (Reading) 157(Pt 4), 1176-1186 (2011).

7. Lumjiaktase, P., Diggle, S.P., Loprasert, S., et al. Quorum sensing regulates dpsA and the oxidative stress response in Burkholderia pseudomallei. Microbiology (Reading) 152(Pt 12), 3651-3659 (2006).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Paraburkholderia tropica (#92647)

Betaproteobacteria (#28216)

Structural characterization of N-acyl-homoserine lactones from bacterial quorum sensing using LC-MS/MS analyses after Paternò-Büchi derivatization in solution.,
Anal Bioanal Chem, 2024

Pubmed ID: 38842688

synthetic construct (#32630)

Synthesis of N-acyl homoserine lactone analogues reveals strong activators of SdiA, the Salmonella enterica serovar Typhimurium LuxR homologue,
Appl Environ Microbiol, 2007

Pubmed ID: 17085703

DOI: 10.1128/AEM.01451-06

InChiKey (Click to copy)

XCZVBYOXRSFQBH-AXDSSHIGSA-N

InChi (Click to copy)

InChI=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

SMILES (Click to copy)

[C@@H]1(CCOC1=O)NC(=O)CC(O)CCCCC

CHEBI ID

182509

PubChem CID

66769741