479050-94-7 Usage
Description
C16-HSL, or N-3-Oxooctadecanoyl-homoserine lactone, is a long-chain molecular signal that plays a crucial role in intercellular communication and regulation of various genetic traits and virulence in many Gram-negative bacteria. It is a member of the N-acyl-homoserine lactones (AHLs) family and is involved in quorum sensing, a process that allows bacteria to sense and respond to changes in their population density. C16-HSL is known for coordinating complex behaviors such as biofilm formation, motility, and the production of virulence factors. Its structure comprises a long chain fatty acyl tail and a lactone ring, and its synthesis is catalyzed by specific enzymes known as AHL synthases. In various bacterial species, C16-HSL can influence gene expression and coordinate collective behaviors, making it a key signaling molecule in bacterial communication and virulence.
Uses
Used in Microbiology Research:
C16-HSL is used as a research tool for studying the mechanisms of bacterial communication, quorum sensing, and gene regulation. It helps researchers understand how bacteria coordinate their behaviors and respond to changes in their environment.
Used in Drug Development:
C16-HSL is used as a target for the development of new antimicrobial agents that can disrupt bacterial communication and virulence. By inhibiting the synthesis or function of C16-HSL, these agents can potentially reduce the pathogenicity of bacteria and treat infections caused by drug-resistant strains.
Used in Biofilm Prevention and Control:
C16-HSL is used as a target for developing strategies to prevent and control biofilm formation in various industrial and medical settings. Since C16-HSL plays a role in coordinating biofilm formation, targeting its synthesis or function can help reduce the formation of biofilms, which are often associated with persistent infections and increased antibiotic resistance.
Used in Environmental Monitoring:
C16-HSL can be used as a biomarker for monitoring the presence and activity of specific bacterial species in various environments. By detecting the levels of C16-HSL, researchers and environmental scientists can gain insights into the population density and behavior of bacteria in different settings, such as water bodies, soil, and air.
Used in Synthetic Biology:
C16-HSL is used as a signaling molecule in synthetic biology applications, where it can be engineered to control the behavior of genetically modified organisms. By incorporating C16-HSL-based quorum sensing systems into synthetic biological circuits, researchers can design bacteria that respond to specific environmental cues and perform desired functions, such as producing biofuels, degrading pollutants, or delivering therapeutic agents.
Check Digit Verification of cas no
The CAS Registry Mumber 479050-94-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,7,9,0,5 and 0 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 479050-94:
(8*4)+(7*7)+(6*9)+(5*0)+(4*5)+(3*0)+(2*9)+(1*4)=177
177 % 10 = 7
So 479050-94-7 is a valid CAS Registry Number.
479050-94-7Relevant articles and documents
Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria
Ziesche, Lisa,Rinkel, Jan,Dickschat, Jeroen S.,Schulz, Stefan
supporting information, p. 1309 - 1316 (2018/06/13)
N-Acylhomoserine lactones (AHLs) are important bacterial messengers, mediating different bacterial traits by quorum sensing in a cell-density dependent manner. AHLs are also produced by many bacteria of the marine Roseobacter group, which constitutes a large group within the marine microbiome. Often, specific mixtures of AHLs differing in chain length and oxidation status are produced by bacteria, but how the biosynthetic enzymes, LuxI homologs, are selecting the correct acyl precursors is largely unknown. We have analyzed the AHL production in Dinoroseobacter shibae and three Phaeobacter inhibens strains, revealing strain-specific mixtures. Although large differences were present between the species, the fatty acid profiles, the pool for the acyl precursors for AHL biosynthesis, were very similar. To test the acyl-chain selectivity, the three enzymes LuxI1 and LuxI2 from D. shibae DFL-12 as well as PgaI2 from P. inhibens DSM 17395 were heterologously expressed in E. coli and the enzymes isolated for in vitro incubation experiments. The enzymes readily accepted shortened acyl coenzyme A analogs, N-pantothenoylcysteamine thioesters of fatty acids (PCEs). Fifteen PCEs were synthesized, varying in chain length from C4 to C20, the degree of unsaturation and also including unusual acid esters, e.g., 2E,11Z-C18:2-PCE. The latter served as a precursor of the major AHL of D. shibae DFL-12 LuxI1, 2E,11Z-C18:2-homoserine lactone (HSL). Incubation experiments revealed that PgaI2 accepts all substrates except C4 and C20-PCE. Competition experiments demonstrated a preference of this enzyme for C10 and C12 PCEs. In contrast, the LuxI enzymes of D. shibae are more selective. While 2E,11Z-C18:2-PCE is preferentially accepted by LuxI1, all other PCEs were not, except for the shorter, saturated C10-C14-PCEs. The AHL synthase LuxI2 accepted only C14 PCE and 3-hydroxydecanoyl-PCE. In summary, chain-length selectivity in AHLs can vary between different AHL enzymes. Both, a broad substrate acceptance and tuned specificity occur in the investigated enzymes.
