l homoserine

L-Homoserine ((S)-(-)-2-AMINO-4-HYDROXYBUTYRIC ACID) 是天然存在的非蛋白丝氨酸，是合成苏氨酸、蛋氨酸和赖氨酸的共有中间体。它是氨基酸丝氨酸的更具反应性的变体。

N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone is a long-chain N-acyl-homoserine lactone (AHL) produced by some Gram-negative bacteria and is involved in quorum sensing. Quorum sensing enables bacteria to change gene expression based on cues from nearby bacteria and from eukaryotic hosts about nutrients, environmental conditions, or threats. Due to the benefit of quorum sensing for bacterial survival, quorum sensing molecules are potential targets for controlling bacterial infections. In mouse and human leukocyte immunoassays using LPS-stimulated macrophages, N-(3-hydroxy-7-cis tetradecenoyl)-L-homoserine lactone did not have an effect on cytokine or antibody production.

L-Homoserine lactone is a synthetic intermediate.1,2It has been used in the synthesis of organoselenium chemistry intermediates and analogs of bacterial quorum-sensing signaling molecules. 1.Koch, T., and Buchardt, O.Synthesis of L-(+)-selenomethionineSynthesis1065-1067(1993) 2.Chhabra, S.R., Harty, C., Hooi, D.S.W., et al.Synthetic analogues of the bacterial signal (quorum seensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulatorsJ. Med. Chem.46(1)97-104(2003)

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) 是由铜绿假单胞菌和洋葱状芽孢杆菌复合物菌株产生的细菌群体感应信号分子，群体感应是细菌用来控制基因表达以响应细胞密度增加的调节系统。N-3-oxo-dodecanoyl-L-Homoserine lactone 诱导 16HBE 人支气管上皮细胞产生 IL-8。

N-(beta-Ketocaproyl)-L-hoMoserine lactone (N-(Ketocaproyl)-L-homoserine lactone) 是群体调节感应的成分之一。

N-3-oxo-hexadecanoyl-L-Homoserine lactone is an unusual, substituted, long-chain N-acyl-homoserine lactone (AHL) produced by some bacteria, including strains of Agrobacterium vitis and Pseudomonas. Like other AHLs, this C16-containing form is thought to be involved in quorum sensing. Substituted, long-chain AHLs, including N-3-oxo-tetradecanoyl-L-homoserine lactone , prime for systemic acquired resistance to pathogen attack in plants.

N-3-oxo-pentanoyl-L-Homoserine lactone is a chain-shortened derivative of the bacterial quorum sensing signaling molecule N-3-oxo-octanoyl-L-homoserine lactone .1It inhibits binding of the autoinducer N-3-oxo-hexanoyl homoserine lactone toE. colicontaining the transcription factor LuxR when used at a concentration of 230 nM.2It acts as an autoinducer to activate theV. fischeriluminescence system inE. coliwhen used at concentrations ranging from 20 to 200 nM. 1.Chhabra, S.R., Stead, P., Bainton, N.J., et al.Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactoneJ. Antibiot. (Tokyo)46(3)441-454(1993) 2.Schaefer, A.L., Hanzelka, B.L., Eberhard, A., et al.Quorum sensing in Vibrio fischeri: Probing autoinducer-LuxR interactions with autoinducer analogsJ. Bacteriol.178(10)2897-2901(1996)

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1] [2] [3] It appears later than shorter acyl chain AHLs in developing biofilms [4] and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, [5] which in turn, inhibits biofilm formation.

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density.[1] This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.[2] 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). 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.[3] C16:1-Δ9-(L)-HSL is a long-chain AHL that functions as a quorum sensing signaling molecule in strains of S. meliloti.[4],[5],[6],[7] Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therapy in the treatment of infectious diseases.[8] Reference：[1]. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol. Mol. Biol. Rev. 70(4), 859-875 (2006).[2]. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J. Bacteriol. 188(2), 773-783 (2006).[3]. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions. FEBS Lett. 580(2), 561-567 (2006).[4]. Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium. Archives of Microbiology 180, 494-497 (2003).[5]. Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti. Journal of Bacteriology 187(23), 7931-7944 (2005).[6]. Marketon, M.M., Glenn, S.A., Eberhard, A., et al. Quorum sensing controls exopolysaccharide production in Sinorhizobium meliloti. Journal of Bacteriology 185(1), 325-331 (2003).[7]. Marketon, M., Gronquist, M.R., Eberhard, A., et al. Characterization of the Sinorhizobium meliloti sinR sinI locus and the production of novel N-Acyl homoserine lactones. Journal of Bacteriology 184(20), 5686-5695 (2002).[8]. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nat. Rev. Microbiol. 6(1), 17-27 (2008).

Quorum sensing is a regulatory process 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). 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. C18:1-δ9 cis-(L)-HSL is a long-chain AHL that may have antimicrobial activity and thus, might be used to inhibit pathogenesis by regulating bacerial quorum sensing signaling.

Quorum sensing is a regulatory process 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). 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. C14:1-δ9-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis. Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.[1] This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.[2] 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.[3] 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.[4] C16-HSL is one of a number of lipophilic, long acyl side-chain bearing AHLs, including its monounsaturated analog C16:1-(L)-HSL, produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in S. meliloti, a nitrogen-fixing bacterial symbiont of certain legumes.[5],[6] C16-HSL is the most abundant AHL produced by the proteobacterium R. capsulatus and activates genetic exchange between R. capsulatus cells.[7] N-Hexadecanoyl-L-homoserine lactone and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.[8],[9]Reference:[1]. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing Microbiol. Mol. Biol. Rev. 70(4), 859-875 (2006).[2]. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry Journal of Bacteriology 188(2), 773-783 (2006).[3]. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies Nature Reviews.Microbiology 6(1), 17-27 (2008).[4]. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions FEBS Letters 580, 561-567 (2006).[5]. Gao, M., Chen, H., Eberhard, A., et al. sinI- and expR-dependent quorum sensing in Sinorhizobium meliloti Journal of Bacteriology 187(23), 7931-7944 (2005).[6]. Teplitski, M., Eberhard, A., Gronquist, M.R., et al. Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium Archives of Microbiology 180, 494-497 (2003).[7]. Schaefer, A.L., Taylor, T.A., Beatty, J.T., et al. Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production Journal of Bacteriology 184(23), 6515-6521 (2002).[8]. Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals Journal of Bacteriology 181(4), 1203-1210 (1999).[9]. Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes Molecular Microbiology 61(4), 839-846 (2006).

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. C18-HSL is one of four lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum sensing signaling in strains of S. meliloti, a nitrogen-fixing bacterial symbiont of the legume M. sativa. C18-HSL and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.

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. C15-HSL is a product of Y. pseudituberculosis.

N-phenylacetyl-L-Homoserine lactone 可衰减病原体鲍曼不动杆菌的群体感应，可用于研究细菌感染。

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-tetradecanoyl-L-Homoserine lactone (C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.[1],[2],[3] It appears later than shorter acyl chain AHLs in developing biofilms[4] and, like other long chain AHLs, stimulates bacterial growth.[5] C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.[6]

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. N-tridecanoyl-L-Homoserine lactone (C13-HSL) possesses a rare odd-numbered acyl carbon chain and is produced by wild-type and mutant strains of Y. pseudotuberculosis in trace amounts.

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.

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Different quorum sensing molecules are produced at different times in bacterial population growth and have distinct cellular effects mediated through changes in gene expression. N-3-hydroxydecanoyl-L-Homoserine lactone is a small diffusible signaling molecule secreted by various bacteria. This lactone is produced via lactonolysis from 3-oxodecanoyl-homoserine lactone, altering quorum sensing or contributing to quorum quenching.

Acetyl-L-homoserine lactone belongs to the family of N-acylated homoserine lactones (HSLs) and has an acyl chain length of two carbons. HSLs perform a role in quorum sensing; however, unlike other HSLs, acetyl-L-homoserine lactone does not elicit a response in bacteria. In an assay of carbapenem antibiotic biosynthesis, acetyl-L-homoserine lactone does not induce a response in E. carotovora. In a fluorescence assay using E. coli containing a reporter plasmid of GFP expression in response to exogenous HSLs, acetyl-L-homoserine does not elicit GFP production.

N-Heptanoyl-L-homoserine lactone 在生命科学相关研究中具有广泛的应用。

Boc-L-Homoserine 是一种有用的有机化合物，可用于生命科学领域的相关研究。其产品编号为 T67363，CAS号为 41088-86-2。

N-(3-Oxodecanoyl)-L-homoserine lactone (3-Oxo-C10-HSL) 作为一种信号分子，在细菌群体感应中充当自诱导分子的角色。

N-3-hydroxyoctanoyl-L-Homoserine lactone, a small diffusible signaling molecule secreted by various bacteria, plays a critical role in quorum sensing—a regulatory system used by bacteria to control gene expression according to cell density changes. This compound is generated via lactonolysis from 3-oxooctanoyl-homoserine lactone and can either activate or suppress gene expression and biofilm formation. Its production and function vary within the bacterial population growth phases, consequently mediating distinct cellular effects through alterations in gene expression, hence contributing to either quorum sensing or quenching.