87206-01-7

Usage

Uses

Used in Bacterial Communication Regulation:
N-hexadecanoyl-L-Homoserine lactone is used as a quorum sensing modulator for regulating and controlling bacterial communication within and between different bacterial species. Its ability to modulate quorum sensing allows it to influence various bacterial behaviors, such as biofilm formation, virulence factor production, and antibiotic resistance.
Used in Microbiology Research:
N-hexadecanoyl-L-Homoserine lactone is used as a research tool for studying the mechanisms of quorum sensing and bacterial communication in various bacterial species. It helps researchers understand the role of acylhomoserine lactones in bacterial populations and their potential applications in controlling bacterial infections and diseases.
Used in Drug Development:
N-hexadecanoyl-L-Homoserine lactone is used as a potential drug candidate for developing new antimicrobial agents targeting bacterial communication and quorum sensing pathways. By disrupting or modulating these pathways, it may be possible to control bacterial infections and reduce the spread of antibiotic-resistant strains.
Used in Biofilm Prevention and Control:
N-hexadecanoyl-L-Homoserine lactone is used as a biofilm prevention and control agent, as it can modulate the quorum sensing pathways involved in biofilm formation. By inhibiting or reducing biofilm formation, it can help prevent bacterial infections and improve the effectiveness of existing treatments.
Used in Agriculture:
N-hexadecanoyl-L-Homoserine lactone is used in agriculture as a plant growth-promoting agent, as it can modulate the communication between plant-associated bacteria and promote beneficial interactions. This can lead to improved plant growth, increased resistance to diseases, and enhanced crop yields.

Upstream product

• 21016-51-3 (R)-S-hexadecanoyl-N-pantothenoylcysteamine 
• 86867-01-8 S-(5’-adenosyl)-L-methionine chloride dihydrochloride 
• 71989-28-1 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine 
• 57-10-3 1-hexadecylcarboxylic acid 

Relevant academic research and scientific papers

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

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.

MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS

The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a l

COMPOUNDS AND METHODS FOR MODULATING COMMUNICATION AND VIRULENCE IN QUORUM SENSING BACTERIA

The present invention provides compositions and methods for modulating the communication and virulence of quorum sensing bacteria. In various exemplary embodiments, the invention provides a combinatorial library of quorum sensing compounds including synthetic analogs of naturally occurring and non-naturally occurring acyl-homoserine lactone (AHL) analogs, and methods of synthesizing and using these compounds.

Small molecule inhibitors of bacterial quorum sensing and biofilm formation

Bacteria monitor their local population densities using small molecules (or autoinducers) in a process known as quorum sensing. Here, we report a new and efficient synthetic route to naturally occurring bacterial autoinducers [N-acyl L-homoserine lactones (AHLs)] that is readily amenable to the synthesis of analogues. This route has been applied in the first synthesis of a library of non-native AHLs. Evaluation of these compounds in bacterial reporter gene and biofilm assays has revealed a potent set of quorum sensing antagonists. These ligands will serve as valuable new tools to explore the role of quorum sensing in bacterial pathogenesis. Copyright