Octanoyl-L-homoserine lactone

Octanoyl-L-homoserine lactone

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Octanoyl-L-homoserine lactone
Category Others
Catalog number BBF-04582
CAS 147852-84-4
Molecular Weight 227.30
Molecular Formula C12H21NO3
Purity >99% by HPLC

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Description

An active quorum sensing modulator first recognised in yersinia pseudotuberculosis. It is produced by the strain of Agrobacterium vitis and Nitrosomonas europeae.

Specification

Synonyms C8-HSL; OHL; N-Octanoyl-L-homoserine lactone; N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide; HTF
Shelf Life 1 Year
Storage Store at -20°C
IUPAC Name N-[(3S)-2-oxooxolan-3-yl]octanamide
Canonical SMILES CCCCCCCC(=O)NC1CCOC1=O
InChI InChI=1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1
InChI Key JKEJEOJPJVRHMQ-JTQLQIEISA-N
Source Synthetic

Properties

Appearance White Solid
Boiling Point 448.1±34.0°C (Predicted)
Melting Point 134-135°C
Density 1.04±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. Identification, synthesis and regulatory function of the N-acylated homoserine lactone signals produced by Pseudomonas chlororaphis HT66
Yi Ouyang, Huasong Peng, Hongbo Hu, Wei Wang, Muhammad Bilal, Xuehong Zhang Microb Cell Fact . 2018 Jan 22;17(1):9. doi: 10.1186/s12934-017-0854-y.
Background:Pseudomonas chlororaphis HT66 isolated from the rice rhizosphere is an important plant growth-promoting rhizobacteria that produce phenazine-1-carboxamide (PCN) in high yield. Phenazine production is regulated by a quorum sensing (QS) system that involves the N-acylated homoserine lactones (AHLs)-a prevalent type of QS molecule.Results:Three QS signals were detected by thin layer chromatography (TLC) and high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS), which identified to be N-(3-hydroxy hexanoyl)-L-homoserine lactone (3-OH-C6-HSL), N-(3-hydroxy octanoyl)-L-homoserine lactone (3-OH-C8-HSL) and N-(3-hydroxy decanoyl)-L-homoserine lactone (3-OH-C10-HSL). The signal types and methods of synthesis were different from that in other phenazine-producing Pseudomonas strains. By non-scar deletion and heterologous expression techniques, the biosynthesis of the AHL-signals was confirmed to be only catalyzed by PhzI, while other AHLs synthases i.e., CsaI and HdtS were not involved in strain HT66. In comparison to wild-type HT66, PCN production was 2.3-folds improved by over-expression of phzI, however, phzI or phzR mutant did not produce PCN. The cell growth of HT66∆phzI mutant was significantly decreased, and the biofilm formation in phzI or phzR inactivated strains of HT66 decreased to various extents.Conclusion:In conclusion, the results demonstrate that PhzI-PhzR system plays a critical role in numerous biological processes including phenazine production.
2. (2R)- and (2S)- 2-hydroxy- hexanoyl and octanoyl-l-homoserine lactones: New highly potent Quorum Sensing modulators with opposite activities
Yves Queneau, Erwann Jeanneau, Laurent Soulère, Qiang Zhang Bioorg Chem . 2020 Nov;104:104307. doi: 10.1016/j.bioorg.2020.104307.
The synthesis and the QS modulation activity of diastereoisomerically pure 2-hydroxy-N-acyl-l-homoserine lactones (2-OH-AHLs) are unveiled. (2R)- and (2S)- 2-hydroxy-N-hexanoyl-l-homoserine lactone and 2-hydroxy-N-octanoyl-l-homoserine lactone have been identified as very potent QS agonists and antagonists on the Vibrio fischeri-quorum sensing system with opposite activities depending on the configuration of the carbon atom with the hydroxyl group. Flexible molecular docking showed that the (2R)-OH configuration in the antagonist isomer induces new hydrogen bonds with Tyr70 and Asp79, two importantly conserved residues in the LuxR protein family, while the (2S)-OH agonist configuration exhibits a binding mode comparable to the natural ligand 3-oxo-hexanoyl-l-homoserine lactone (OHHL). For the analogs with long alkyl chain 3a and 3b and aromatic analogs, all are antagonists with no effect of the configuration at C-2.
3. Human TRPV1 and TRPA1 are receptors for bacterial quorum sensing molecules
Naoya Tobita, Kana Tsuneto, Shigeaki Ito, Takeshi Yamamoto J Biochem . 2022 Jan 7;170(6):775-785. doi: 10.1093/jb/mvab099.
In this study, we investigated the activation of TRPV1 and TRPA1 by N-acyl homoserine lactones, quorum sensing molecules produced by Gram-negative bacteria, and the inhibitory effect of TRPV1 and TRPA1 by autoinducing peptides (AIPs), quorum sensing molecules produced by Gram-positive bacteria, using human embryonic kidney 293T cell lines stably expressing human TRPV1 and TRPA1, respectively. As a result, we found that some N-acyl homoserine lactones, such as N-octanoyl-L-homoserine lactone (C8-HSL), N-nonanoyl-L-homoserine lactone (C9-HSL) and N-decanoyl-L-homoserine lactone (C10-HSL), activated both TRPV1 and TRPA1. In addition, we clarified that some N-acyl homoserine lactones, such as N-3-oxo-dodecanoyl-L-homoserine lactone (3-oxo-C12-HSL), only activated TRPV1 and N-acyl homoserine lactones having saturated short acyl chain, such as N-acetyl-L-homoserine lactone (C2-HSL) and N-butyryl-L-homoserine lactone (C4-HSL), only activated TRPA1. Furthermore, we found that an AIP, simple linear peptide CHWPR, inhibited both TRPV1 and TRPA1 and peptide having thiolactone ring DICNAYF, the thiolactone ring were formed between C3 to F7, strongly inhibited only the TRPV1. Although the specificity of TRPV1 and TRPA1 for quorum sensing molecules was different, these data suggest that both TRPV1 and TRPA1 would function as receptors for quorum sensing molecule produced by bacteria. Graphical Abstract.

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