Acetyl-L-homoserine lactone

Acetyl-L-homoserine lactone

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Acetyl-L-homoserine lactone
Category Others
Catalog number BBF-04200
CAS 51524-71-1
Molecular Weight 143.14
Molecular Formula C6H9NO3
Purity >99% by HPLC

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Description

It is the shortest and most polar alkyl homologue of a family of mediators of cell to cell interactions in bacterial biofilms. It can cause carbapenem formation in Erwinia carotovora.

Specification

Synonyms C2-HSL; N-Acetyl-L-homoserine lactone; N-Ethanoyl-L-homoserine lactone; Acetylhomoserine lactone; N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-acetamide
Storage Store at -20°C
IUPAC Name N-[(3S)-2-oxooxolan-3-yl]acetamide
Canonical SMILES CC(=O)NC1CCOC1=O
InChI InChI=1S/C6H9NO3/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)/t5-/m0/s1
InChI Key XGSXMDQVYYCSDA-YFKPBYRVSA-N
Source Synthetic

Properties

Appearance White Solid
Boiling Point 441.3±34.0°C (Predicted)
Melting Point 113-117°C
Density 1.20±0.1 g/cm3 (Predicted)
Solubility Slightly soluble in Chloroform, DMF (Sparingly), Methanol (Sonicated)

Reference Reading

1. Piscirickettsia salmonis Produces a N-Acetyl-L-Homoserine Lactone as a Bacterial Quorum Sensing System-Related Molecule
Cristian Oliver, Pamela Ruiz, David Contreras, Nathaly Ruiz-Tagle, Javier Barros, Alex Romero, Romina Romero, Carlos Carrasco, Homero Urrutia, Daniela Sepulveda, José Miguel Vidal Front Cell Infect Microbiol . 2021 Oct 25;11:755496. doi: 10.3389/fcimb.2021.755496.
Piscirickettsia salmonisis the etiological agent of piscirickettsiosis, the most prevalent disease in salmonid species in Chilean salmonids farms. Many bacteria produceN-acyl-homoserine lactones (AHLs) as a quorum-sensing signal molecule to regulate gene expression in a cell density-dependent manner, and thus modulate physiological characteristics and several bacterial mechanisms. In this study, a fluorescent biosensor system method and gas chromatography-tandem mass spectrometry (GC/MS) were combined to detect AHLs produced byP. salmonis.These analyses revealed an emitted fluorescence signal when the biosensorP. putidaEL106 (RPL4cep) was co-cultured with both,P. salmonisLF-89 type strain and an EM-90-like strain Ps007, respectively. Furthermore, the production of an AHL-type molecule was confirmed by GC/MS by bothP. salmonisstrains, which identified the presence of a N-acetyl-L-homoserine Lactone in the supernatant extract. However, It is suggested that an alternate pathway could synthesizes AHLs, which should be address in future experiments in order to elucidate this important bacterial process. To the best of our knowledge, the present report is the first to describe the type of AHLs produced byP. salmonis.
2. 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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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