| Identification | Back Directory | [Name]
N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone | [CAS]
273734-65-9 | [Synonyms]
(S)-N-3-hydroxy-(7Z)-tetradecenoyl-homoserine lactone
N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone | [Molecular Formula]
C18H31NO4 | [MOL File]
273734-65-9.mol | [Molecular Weight]
325.44 |
| Hazard Information | Back Directory | [Description]
N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone is a long-chain N-acyl-homoserine lactone (AHL) produced by some Gram-negative bacteria and is involved in quorum sensing.1 Quorum sensing enables bacteria to change gene expression based on cues from nearby bacteria and from eukaryotic hosts about nutrients, environmental conditions, or threats.2 Due to the benefit of quorum sensing for bacterial survival, quorum sensing molecules are potential targets for controlling bacterial infections.3 In mouse and human leukocyte immunoassays using LPS-stimulated macrophages, N-(3-hydroxy-7-cis tetradecenoyl)-L-homoserine lactone did not have an effect on cytokine or antibody production.4 | [Definition]
ChEBI: N-(3-Hydroxy-7-cis-tetradecenoyl)homoserine lactone is a N-acyl-amino acid. | [References]
1. Laue, B.E., Jiang, Y., Chhabra, S.R., et al. The biocontrol strain Pseudomonas fluorescens F113 produces the Rhizobium small bacteriocin, N-(3-hydroxy-7-cis-tetradecenoyl)homoserine lactone, via HdtS, a putative novel N-acylhomoserine lactone synthase Microbiology 146 (Pt. 10),2469-2480(2000).
2. Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world Microbiology 153 (Pt 12),3923-3938(2007).
3. Meng, L.J., and Sj?vall, J. Method for combined analysis of profiles of conjugated progesterone metabolites and bile acids in serum and urine of pregnant women J. Chromatogr. B Biomed. Sci. Appl. 688(1),11-26(1997).
4. Telford, G., Wheeler, D., Williams, P., et al. The Pseudomonas aeruginosa quorum-sensing signal molecule N-(3-oxododecanoyl)-L-homoserine lactone has immunomodulatory activity Infect. Immun. 66(1),36-42(1998). |
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