147852-83-3 Usage
Description
N-hexanoyl-L-homoserine lactone, also known as AHL, is a small diffusible signaling molecule produced and utilized by various Gram-negative bacteria as a quorum sensing (QS) signal molecule. It plays a crucial role in controlling gene expression, affecting cellular metabolism, and regulating virulence in bacteria.
Uses
Used in Medical Applications:
N-hexanoyl-L-homoserine lactone is used as a quorum sensing modulator for controlling bacterial infections, particularly in cystic fibrosis patients. By interfering with the quorum sensing systems, it can help reduce the severity of infections and improve patient outcomes.
Used in Commercial Agriculture:
N-hexanoyl-L-homoserine lactone is used as a biofilm reduction agent to prevent the formation of harmful biofilms on crops and in agricultural settings. This application can lead to increased crop yields and reduced reliance on chemical treatments.
Used in Aquaculture:
In the aquaculture industry, N-hexanoyl-L-homoserine lactone is used as an infection prevention agent. By modulating the quorum sensing systems in bacteria, it can help reduce the occurrence of septicemia in fish and other aquatic organisms, leading to healthier and more productive aquatic ecosystems.
Used in Food Industry:
N-hexanoyl-L-homoserine lactone is used as a food spoilage prevention agent. By controlling the quorum sensing systems in bacteria responsible for spoilage, it can help extend the shelf life of perishable foods and reduce food waste.
Used in Research:
N-hexanoyl-L-homoserine lactone is used as a research tool for studying the mechanisms of bacterial communication and regulation. Understanding the role of this molecule in quorum sensing can lead to the development of new strategies for controlling bacterial infections and improving public health.
Biochem/physiol Actions
N-Hexanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.
Check Digit Verification of cas no
The CAS Registry Mumber 147852-83-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,7,8,5 and 2 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 147852-83:
(8*1)+(7*4)+(6*7)+(5*8)+(4*5)+(3*2)+(2*8)+(1*3)=163
163 % 10 = 3
So 147852-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)/t8-/m0/s1
147852-83-3Relevant articles and documents
Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators
Sabbah, Mohamad,Fontaine, Fanny,Grand, Lucie,Boukraa, Mohamed,Efrit, Mohamed L.,Doutheau, Alain,Soulere, Laurent,Queneau, Yves
scheme or table, p. 4727 - 4736 (2012/08/29)
New analogues of N-acyl-homoserine-lactone (AHL), in which the amide was replaced by a triazole or tetrazole ring, were prepared and tested for their activity as LuxR-dependent QS modulators. Several compounds showed a level of antagonistic or agonistic activity, notably some 1,4-triazolic and 1,5-tetrazolic derivatives, whereas the 2,5-tetrazolic compounds were inactive. In 1,5-tetrazoles, substituted with butyrolactone and an alkyl chain, the activity was reversed, depending on the connection between the lactone and the tetrazole. The C-N connected compounds were agonists whereas the C-C connected ones were antagonists.
Acyl-homoserine lactones from Erwinia psidii R. IBSBF 435T, a guava phytopathogen (Psidium guajava L.)
Pomini, Armando M.,Manfio, Gilson P.,Araujo, Welington L.,Marsaioli, Anita J.
, p. 6262 - 6265 (2007/10/03)
The phytopathogen Erwinia psidii R. IBSBF 435T causes rot in branches, flowers, and fruits of guava (Psidium guajava L.), being responsible for crop losses, and has no effective control. It was demonstrated that this strain produces two compounds [S-(-)-N-hexanoyl and N-heptanoyl-homoserine lactone], both belonging to the class of quorum-sensing signaling substances. A protocol using gas chromatography - flame ionization detection with chiral stationary phase is described for the absolute configuration determination of a natural acyl-homoserine lactone. Biological assays with specific reporter and synthesis of identified substances are also described. This is the first report on the N-heptanoyl-homoserine lactone occurrence in the Erwinia genus.
