Decanoyl-L-homoserine lactone
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| Category | Others |
| Catalog number | BBF-04422 |
| CAS | 177315-87-6 |
| Molecular Weight | 255.35 |
| Molecular Formula | C14H25NO3 |
| Purity | >99% by HPLC |
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Description
An active quorum sensing modulator first recognised in burkholderia pseudomallei. It is detected in hundreds of bacterial species.
Specification
| Synonyms | C10-HSL; N-Decanoyl-L-homoserine lactone; N-[(3S)-2-Oxotetrahydrofuran-3-yl]decanamide |
| Storage | Store at -20°C |
| IUPAC Name | N-[(3S)-2-oxooxolan-3-yl]decanamide |
| Canonical SMILES | CCCCCCCCCC(=O)NC1CCOC1=O |
| InChI | InChI=1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)/t12-/m0/s1 |
| InChI Key | TZWZKDULKILUPV-LBPRGKRZSA-N |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Boiling Point | 466.1±34.0°C (Predicted) |
| Melting Point | 127-130°C |
| Density | 1.02±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. 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.
2. 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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
