| Identification | Back Directory | [Name]
N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE | [CAS]
216596-71-3 | [Synonyms]
C11-HSL
N-UNDECANOYL-L-HOMOSERINE LACTONE
N-[(3S)-2-oxooxolan-3-yl]undecanamide
N-[(3S)-TETRAHYDRO-2-OXO-3-FURANYL]-UNDECANAMIDE
Undecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]- | [Molecular Formula]
C15H27NO3 | [MDL Number]
MFCD11976916 | [MOL File]
216596-71-3.mol | [Molecular Weight]
269.38 |
| Hazard Information | Back Directory | [Description]
Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C11-HSL possesses a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in P. aeruginosa strains. | [Uses]
Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial research for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains. | [storage]
Store at -20°C | [References]
[1] MICHAIL SYRPAS. Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators.[J]. Beilstein Journal of Organic Chemistry, 2014: 2539-2549. DOI: 10.3762/bjoc.10.265
[2] SIRI RAM CHHABRA. Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone as Immune Modulators[J]. Journal of Medicinal Chemistry, 2002, 46 1: 97-104. DOI: 10.1021/jm020909n
[3] LéA GIRARD. Characterization of N-Acyl Homoserine Lactones in Vibrio tasmaniensis LGP32 by a Biosensor-Based UHPLC-HRMS/MS Method.[J]. Sensors (Basel, Switzerland), 2017. DOI: 10.3390/s17040906 |
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